Herbicidal tricyclic heterocycles

ABSTRACT

Compounds of Formula I having herbicidal utility are disclosed: ##STR1## wherein Q, R 1 , R 2 , V, m and p are defined in the text, including compositions containing such compounds, and a method for controlling weeds employing such compounds.

This is a national filing of PCT/US Ser. No. 95/01502, filed 10 Feb., 1995, which is a continuation-in-part of U.S. Ser. No. 08/197,085, filed 16 Feb., 1994, now abandoned.

BACKGROUND OF THE INVENTION

This invention comprises tricyclic imides, pyrazoles, and triazolones, and bicyclic ureas wherein one of the rings is a fused cyclopropane, and their agriculturally-suitable salts, for weed control in crops.

EP-A-493,323 discloses bicyclic imide herbicides, WO 93/15074 discloses bicyclic pyrazole herbicides, and U.S. Pat. No. 4,213,773 discloses bicyclic triazolone herbicides, but they lack the fused cyclopropane ring present in the compounds of this invention.

SUMMARY OF THE INVENTION

The compounds of this invention are compounds of Formulae I-IV: ##STR2## wherein Q is ##STR3## R¹ is independently hydrogen; halogen or C₁ -C₃ alkyl; R² is independently hydrogen; fluorine; chlorine; or bromine;

V is O or S;

X is halogen or cyano;

m is 1 or 2;

p is 0 or 1 provided that when m is 2, then p is 0;

W is O or S;

R³ is halogen;

R⁴ is H; C₁ -C₈ alkyl; C₁ -C₈ haloalkyl; halogen; OH; OR⁹ ; SH; S(O)_(n) R⁹ ; COR⁹ ; CO₂ R⁹ ; C(O)SR⁹ ; C(O)NR¹¹ R¹² ; CHO; CR¹¹ ═NOR¹⁸ ; CH═CR¹⁹ CO₂ R⁹ ; CH₂ CHR¹⁹ CO₂ R⁹ ; CO₂ N═CR¹³ R¹⁴ ; NO₂ ; CN; NHSO₂ R¹⁵ ; NHSO₂ NHR¹⁵ ; NR⁹ R²⁰ ; NH₂ or phenyl optionally substituted with R²¹ ;

n is 0, 1 or 2;

R⁵ is C₁ -C₂ alkyl; C₁ -C₂ haloalkyl; OCH₃ ; SCH₃ ; OCHF₂ ; halogen; CN or NO₂ ;

R⁶ is H; C₁ -C₃ alkyl or halogen;

R⁷ is H; C₁ -C₃ alkyl; halogen; C₁ -C₃ haloalkyl; cyclopropyl; vinyl; C₂ alkynyl; CN; C(O)R²⁰ ; CO₂ R²⁰ ; C(O)NR²⁰ R²² ; CR¹⁶ R¹⁷ CN; CR¹⁶ R¹⁷ C(O)R²⁰ ; CR¹⁶ R¹⁷ CO₂ R²⁰ ; CR¹⁶ R¹⁷ C(O)NR²⁰ R²² ; CHR¹⁶ OH; CHR¹⁶ OC(O)R²⁰ or OCHR¹⁶ OC(O)NR²⁰ R²² ; or when Q is Q-2, R⁶ and R⁷ can be taken together with the carbon to which they are attached to form C═O;

R⁸ is H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkoxyalkyl; C₃ -C₆ alkenyl; C₃ -C₆ alkynyl; C₄ -C₇ cycloalkyalkyl; ##STR4## R⁹ is C₁ -C₈ alkyl; C₃ -C₈ cycloalkyl; C₃ -C₈ alkenyl; C₃ -C₈ alkynyl; C₁ -C₈ haloalkyl; C₂ -C₈ alkoxyalkyl; C₂ -C₈ alkylthioalkyl; C₂ -C₈ alkylsulfinylalkyl; C₂ -C₈ alkylsulfonylalkyl; C₄ -C₈ alkoxyalkoxyalkyl; C₄ -C₈ cycloalkylalkyl; C₆ -C₈ cycloalkoxyalkyl; C₄ -C₈ alkenyloxyalkyl; C₄ -C₈ alkynyloxyalkyl; C₃ -C₈ haloalkoxyalkyl; C₄ -C₈ haloalkenyloxyalkyl; C₄ -C₈ haloalkynyloxyalkyl; C₆ -C₈ cycloalkylthioalkyl; C₄ -C₈ alkenylthioalkyl; C₄ -C₈ alkynylthioalkyl; C₁ -C₄ alkyl substituted with phenoxy or benzyloxy, each ring optionally substituted with halogen, C₁ -C₃ alkyl or C₁ -C₃ haloalkyl; C₄ -C₈ trialkylsilylalkyl; C₃ -C₈ cyanoalkyl; C₃ -C₈ halocycloalkyl; C₃ -C₈ haloalkenyl; C₅ -C₈ alkoxyalkenyl; C₅ -C₈ haloalkoxyalkenyl; C₅ -C₈ alkylthioalkenyl; C₃ -C₈ haloalkynyl; C₅ -C₈ alkoxyalkynyl; C₅ -C₈ haloalkoxyalkynyl; C₅ -C₈ alkylthioalkynyl; C₂ -C₈ alkylcarbonyl; benzyl optionally substituted with halogen, C₁ -C₃ alkyl or C₁ -C₃ haloalkyl; CHR¹⁶ COR¹⁰ ; CHR¹⁶ P(O)(OR¹⁰)₂ ; CHR¹⁶ P(S)(OR¹⁰)₂ ; P(O)(OR¹⁰)₂ ; P(S)(OR¹⁰)₂ ; CHR¹⁶ C(O)NR¹¹ R¹² ; CHR¹⁶ C(O)NH₂ ; CHR¹⁶ CO₂ R¹⁰ ; CO₂ R¹⁰ ; SO₂ R¹⁰ ; phenyl optionally substituted with R²¹ ; ##STR5## R¹⁰ is C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₃ -C₆ alkenyl or C₃ -C₆ alkynyl;

R¹¹ and R¹³ are independently H or C₁ -C₄ alkyl;

R¹² and R¹⁴ are independently C₁ -C₄ alkyl or phenyl optionally substituted with halogen, C₁ -C₃ alkyl or C₁ -C₃ haloalkyl; or

R¹¹ and R¹² are taken together along with the nitrogen to which they are attached to form a piperidinyl, pyrrolidinyl or morpholinyl ring, each ring optionally substituted with C₁ -C₃ alkyl, phenyl or benzyl; or

R¹³ and R¹⁴ are taken together with the carbon to which they are attached to form C₃ -C₈ cycloalkyl;

R¹⁵ is C₁ -C₄ alkyl or C₁ -C₄ haloalkyl;

R¹⁶ and R¹⁷ are independently H or C₁ -C₅ alkyl;

R¹⁸ is H, C₁ -C₆ alkyl, C₃ -C₆ alkenyl or C₃ -C₆ alkynyl;

R¹⁹ and R²⁴ are independently H, C₁ -C₄ alkyl or halogen; or

R⁹ and R¹⁹ are taken together as C₂ -C₃ alkylene;

R²⁰, R²¹, and R²⁵ are independently H or C₁ -C₄ alkyl;

R²² is C₁ -C₂ alkyl; C₁ -C₂ haloalkyl; OCH₃ ; SCH₃ ; OCHF₂ ; halogen; CN or NO₂ ; and

R²³ is H; C₁ -C₅ alkyl; C₁ -C₅ haloalkyl; C₃ -C₆ cycloalkyl; C₃ -C₆ halocycloalkyl; and phenyl optionally substituted with up to three substituents independently selected from the group halogen, NO₂, cyano, C₁ -C₂ alkyl, C₁ -C₂ haloalkyl, C₁ -C₂ alkoxy, and C₁ -C₂ haloalkoxy;

and their corresponding N-oxides and agriculturally suitable salts.

Preferred compounds of Formulae I-IV for reasons including ease of synthesis and/or greater herbicidal efficacy are:

1. A compound of Formulae I-IV wherein

R¹ is hydrogen or halogen;

R² is hydrogen; chlorine; or fluorine;

R⁴ is H; C₁ -C₈ alkyl; C₁ -C₈ haloalkyl; halogen; OH; OR⁹ ; SH; S(O)_(n) R⁹ ; COR⁹ ; CO₂ R⁹ ; C(O)SR⁹ ; C(O)NR¹¹ R¹² ; CHO; CH═CHCO₂ R⁹ ; CO₂ N═CR¹³ R¹⁴ ; NO₂ ; CN; NHSO₂ R¹⁵ ; or NHSO₂ NHR¹⁵ ; and

R²³ is C₁ -C₂ alkyl.

2. Compounds of Preferred 1 wherein

R² is hydrogen or fluorine; and

R⁹ is C₁ -C₄ alkyl; C₃ -C₄ alkenyl; C₃ -C₄ alkynyl; C₂ -C₄ alkoxyalkyl; C₁ -C₄ haloalkyl; C₃ -C₄ haloalkenyl or C₃ -C₄ haloalkynyl.

3. Compounds of Preferred 2 wherein

Q is Q-1 or Q-5;

R¹ and R² are each hydrogen; and

R⁵ is halogen; CN; or NO₂.

Specifically preferred is a compound of Preferred 3 selected from the group:

(±)-2- 4-chloro-2-fluoro-5-(2-propynyloxy)phenyl!tetrahydrocyclopropa 3,4!-pyrrolo 1,2-c!imidazole-1,3(2H,3aH)-dione and (±)-2- 4-chloro-2-fluoro-5- (1-methyl-2-propynyl)oxy!phenyl!tetrahydrocyclopropa 3,4!-pyrrolo 1,2-c!imidazole-1,3(2H,3aH)-dione.

Another embodiment of the invention is an agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of Formulae I-IV with the substituents as defined above.

A further embodiment of the invention is a method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of Formulae I-IV with the substituents as defined above.

DETAILS OF THE INVENTION

Compounds of Formulae I-IV may exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be the more active. One skilled in the art knows how to separate said enantiomers, diastereomers and geometric isomers. Accordingly, the present invention comprises racemic mixtures, individual stereoisomers, and optically active mixtures.

In the above recitations, the term "alkyl" used either alone or in compound words such as "alkylthio" includes straight or branched alkyl such as methyl, ethyl, n-propyl, isopropyl and the different butyl, pentyl and hexyl isomers. Examples of "alkylsulfonyl" include CH₃ S(O)₂, CH₃ CH₂ S(O)₂, CH₃ CH₂ CH₂ S(O)₂, (CH₃)₂ CHS(O)₂ and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. Alkoxy includes methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. Alkenyl includes straight or branched chain alkenes such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. "Alkenyloxy" includes straight-chain or branched alkenyloxy moieties, examples include H₂ C═CHCH₂ O, (CH₃)₂ C═CHCH₂ O, (CH₃)CH═CHCH₂ O, (CH₃)CH═C(CH₃)CH₂ O and CH₂ ═CHCH₂ C₂ O. "Alkynyloxy" includes straight-chain or branched alkynyloxy moieties, examples include HC.tbd.CCH₂ O, CH₃ C.tbd.CCH₂ O and CH₃ C.tbd.CCH₂ CH₂ O. Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The term "halogen", either alone or in a compound word such as "haloalkyl", denotes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl", said alkyl can be partially or fully substituted with independently selected halogen atoms. Examples of haloalkyl include CH₂ CH₂ F, CF₂ CF₃ and CH₂ CHFCl.

The total number of carbon atoms in a substituent group is indicated by the "C_(i) -C_(j) " prefix where i and j are numbers from 1 to 8. For example, C₄ alkoxy designates the various isomers of an alkoxy group containing a total of 4 carbon atoms, examples including OCH₂ CH₂ CH₂ CH₃, OCH₂ CH(CH₃)₂, OC(CH₃)₃.

The compounds represented by Formulae I-IV can be prepared according to the methods illustrated below in Schemes 1-13. The definitions of Q, X, m, p, W, n, and R¹ through R²⁵ in the compounds of Formulae 1-15 below are as defined above in the Summary of the Invention.

As illustrated in Scheme 1, treatment of the cis-cyclopropane dicarboxylic acid of Formula 1 with urea and heating to 175°-185° C. affords the cis-dicarboximide of Formula 2 as described by G. C. Crockett et al. in Synth. Commun. (1981), 11, 447-454. ##STR6##

The diester of the diacid of Formula 1 is prepared by the method described by L. L. McCoy in J. Am. Chem. Soc., (1958), 80, 65-68. A mixture of cis- and trans-diesters are obtained and the desired cis-isomer can be isolated by chromatography. The cis-diacid can be obtained by saponification of the diester using well-known methods.

Reduction of the cis-dicarboximide of Formula 2 with borane in an inert solvent, such as tetrahydrofuran (THF), followed by work-up with aqueous hydrochloric acid affords the azabicyclo 3.1.0!hexane hydrochloride of Formula 3 (Scheme 2). The reduction is preferably conducted with heating, for example in THF at reflux, as described by H. C. Brown and P. Heim in J. Org. Chem., (1973), 38, 912-916. ##STR7##

Alternatively, compounds of Formula 3 can be obtained by the cyclopropanation method (Scheme 3) described by B. Withop et al; in J. Am. Chem. Soc. (1971) 94, 3471-3477. ##STR8##

The amine hydrochloride of Formula 3 is converted via a five step sequence to the α-aminoacid of Formula 7 as illustrated in Scheme 4. Purification of the intermediates is not necessary. ##STR9##

Neutralization of the amine hydrochloride with a base, such as concentrated aqueous potassium hydroxide, liberates the free amine. Dissolution of the amine in an inert solvent, such as diethyl ether, and treatment with a solution of N-chlorosuccinimide (NCS) in an inert solvent such as ether, produces the chloramine of Formula 4. The solution of the chloramine is then treated with ethanolic potassium hydroxide to effect dehydrochlorination and give the imine of Formula 5. Once again, the imine is not purified but treated directly first with aqueous sodium bisulfite, and then with solid sodium cyanide to afford the aminonitrile of Formula 6. The reaction mixture is poured into water and extracted with a water-immiscible solvent such as ether. The organic layers are dried and evaporated under reduced pressure to afford the aminonitrile. No additional purification is necessary. The aminonitrile of Formula 6 can be converted to the aminoacid of Formula 7 by hydrolysis with aqueous barium hydroxide followed by neutralization with sulfuric acid. A mixture of epimers at the carboxylic acid centers is obtained, and the individual diastereomers can be separated by chromatography.

Amides of Formula 9 can be prepared as outlined in Scheme 5. The acid of Formula 7 is reacted with an aniline of Formula 8 and a trialkylaluminum reagent (e.g., trimethylaluminum), in a non-coordinating solvent such as an aromatic hydrocarbon (e.g., benzene and toluene) or halogenated hydrocarbon (e.g., methylene chloride, chloroform, carbon tetrachloride, and dichlorobutane) to obtain the amide. Generally, the reaction requires 0.1 to 48 hours at a temperature of 0° C. to 25° C. to proceed to completion. The amides of Formula 9 are isolated by extraction into an organic solvent, aqueous wash, and removal of the solvent under reduced pressure. Purification can be accomplished by chromatography or recrystallization. Anilines of Formula 8 are known or can be prepared by known methods. For example, the synthesis of anilines of Formula 9 wherein Q is Q-1, Q-4, and Q-5 is described in U.S. Pat. No. 4,902,335. The anilines wherein Q is Q-2 and Q-3 can be prepared as described in U.S. Pat. No. 5,053,071 or by well known modifications thereof. ##STR10##

The reaction illustrated in Scheme 5 can also be performed starting with the ester of the acid of Formula 7.

In addition, amides of Formula 9 can be generated using conventional 1,3-dicyclohexylcarbodiimide (DCC) procedures for coupling N-protected compounds of Formula 10 with amines of Formula 8 followed by removal of the protecting group according to the procedures outlined by Bodanszky, M. in Principles of Peptide Synthesis, Volume 16, Springer-Verlag, New York, (1984) (Scheme 6). ##STR11##

The tricyclic imide of Formula I can be prepared from the α-aminoamide of Formula 9 by condensation with thiophosgene, phosgene (U═Cl) or a phosgene equivalent as illustrated in Scheme 7. Treatment of the α-aminoamide with (thio)phosgene is preferably carried out in the presence of a tertiary-amine base such as triethylamine, pyridine, or N,N-diisopropylethylamine, in an inert solvent such as dichloromethane or 1-chlorobutane. The phosgene can be added as a gas or as a solution in an inert solvent such as toluene. Suitable temperatures range from about 0° C. to the reflux temperature of the solvent. Diphosgene (ClC(═O)OCCl₃) and triphosgene (Cl₃ COC(═O)OCCl₃) can also be used in a similar manner. ##STR12##

Alternatively, the imides of Formula I where V═O can be prepared using 1,1'-carbonyldiimidazole (U=1-imidazolyl, CDI). The amide of Formula 9 is dissolved in an inert solvent in which the CDI has sufficient solubility at the reaction temperature. Methylene chloride, 1-chlorobutane and toluene are three of many suitable inert solvents. The CDI is added as a solid or as a solution in an inert solvent at temperatures from 0° C. to 100° C. When the reaction is complete, the resulting mixture is poured into a water-immiscible solvent and washed successively with dilute mineral acid, water, and brine. The organic liquid phase is separated, dried, and evaporated to isolate the product.

Compounds of Formula I can also be prepared by treating amides of Formula 9 with 1,1'-carbonylditriazole (U=1,2,4-triazolyl, CDT) as described above for CDI. Additional base can be added to accelerate the reaction. Suitable bases include a trialkylamine, imidazole, pyridine, picoline or other substituted pyridine, or mixtures thereof. For both CDI and CDT, the carbonylating agent can be added as a pure compound, or as a solution of the pure compound in an inert solvent. For example, CDI can be first prepared by treatment of a solution of imidazole in an inert solvent with phosgene as described by Staab and Wendel (Org. Syntheses, Coll. Vol. 5, 201, (1973)), and then treated in situ with the amide of Formula 9 to afford I.

Compounds of Formula I can also be prepared from compounds of Formula II when R²³ ═H as shown in Scheme 8. ##STR13##

Intramolecular cyclization of II to give compounds in Formula I can be effected by heating II at elevated temperature between 5° C. to 200° C. in suitable inert organic solvents, e.g., an aromatic hydrocarbon such as benzene or toluene.

Compounds of Formula II can be prepared by first converting amines of Formula 8 to isocyanates or thiocyanates of Formula 10 using conventional diphosgene, triphosgene, or thiophosgene reaction with amines (Scheme 9). Generally, the triphosgene or the thiophosgene is contacted with amines as compound 8 at low temperature 0°-25° C. in the presence of a suitable base such as a tertiary amine, e.g., pyridine or triethylamine (with hydrocarbon solvents, e.g., toluene, chlorinated alkane such as chloroform or methylene chloride). ##STR14##

Compounds of Formula II can be obtained by contacting compounds of Formula 10 with compounds of Formula 3 (Scheme 10) ##STR15##

The reaction is run in a suitable organic solvent, e.g., chlorinated alkane such as chloroform or methylene chloride, an aromatic hydrocarbon such as benzene or toluene, or an ether type solvent such as THF. For completion of the reaction, it is sometimes necessary to heat the reaction mixture to reflux.

The tricyclic imides of Formula I and bicyclic ureas of Formula II can be isolated by extraction into an organic solvent, aqueous wash, and removal of the solvent under reduced pressure. Additional purification can be accomplished by chromatography or recrystallization.

Compounds of Formula III can be made by the reaction of sydnones of Formula 11 with appropriately substituted alkynes 12 (Scheme 11). ##STR16##

The reaction takes place at elevated temperatures generally between 80° C. and 200° C. The reaction may be performed in a variety of solvents with aromatic hydrocarbons such as xylenes preferred.

The sydnones of Formula 11 can be made using procedures known in the art (see S. D. Larsen and E. Martinsorough, Tetrahedron Lett. 1989, 4625 and D. Ranganathan and S. Bamezai, Tetrahedron Lett. 1983, 1067).

Scheme 12 shows how compounds of Formula III can also be prepared by coupling compounds of Formula 13, with aryl halides or sulfonates 14 in the presence of palladium catalysts as described by Yamanoka et al., Heterocycles, 33, 813-818 (1992). Compounds of Formula 13, can be made by sydnone cycloaddition as described in Scheme 11 using stannylated acetylenes. ##STR17##

The compounds in Formula IV may be made as shown in Scheme 13. ##STR18##

The conversion of the amidrazones 15, or their acid salts (e.g., hydrochlorides), to the compounds of Formula IV is accomplished by reaction with either diphosgene, triphosgene or thiophosgene. The reaction is run in a suitable inert organic solvent, e.g., benzene, toluene, CHCl₃ or CH₂ Cl₂ with a suitable base such as pyridine or a tertiary amine, e.g., Et₃ N. The product of the reaction can be isolated by extraction into organic solvent, aqueous wash, and removal of the solvent under reduced pressure. Purification of the crude material is accomplished by standard techniques, e.g., crystallization, chromatography or distillation.

The amidrazones 15, may be prepared by methods similar to those described in U.S. Pat. No. 4,213,773.

It is recognized that some reagents and reaction conditions described above for preparing compounds of Formulae I-IV may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences into the synthesis will aid in obtaining the desired products. The use and choice of the protecting group will be apparent to one skilled in chemical synthesis.

In the following Examples, all ¹ H NMR spectra were measured in CDCl₃ solution at 300 MHz unless otherwise indicated.

EXAMPLE 1 Preparation of (±)-2- 4-chloro-2-fluoro-5-(2-propynyloxy)phenyl!tetrahydrocyclopropa 3,4!pyrrolo 1,2-c!imidazole-1,3(2H,3aH)-dione

Step A

Preparation of diethyl cis-1,2-cyclopropanedicarboxylate

To a stirred suspension of 32.8 g (818.8 mmol) of 60% sodium hydride mineral oil dispersion in 200 mL of toluene under nitrogen, was added between 10 to 20 mL of a blend of ethyl acrylate (81.2 g, 810.7 mmol) and ethyl chloroacetate (99.4 g, 810.7 mmol) followed by several drops of ethanol. After an induction period of about 1 h, steady gas and heat evolution began with the reaction mixture temperature reaching 35° C. The remaining mixed ester reagent was carefully added dropwise with ice-bath cooling so as to maintain a reaction temperature of 30°-80° C. After the addition was complete (4 h), the mixture was cooled to room temperature and carefully poured into water (300 mL). The organic layer was separated and dried (MgSO₄) and evaporated to a dry residue. The dry residue was chromatographed on silica gel using 10% ethyl acetate in hexane as the eluant. The fractions containing the desired compound were combined and evaporated to dryness under reduced pressure to give 53.0 g of the title compound of Step A as a clear oil (35% yield). IR (neat, cm⁻¹): 1728.9 (C═O);

¹ H NMR: δ4.20-4.12 (m,4H), 2.14-2.05 (t,2H), 1.71-1.62 (q,1H), 1.31-1.20 (m,7H).

Step B

Preparation of cis-1,2-cyclopropanedicarboxylic acid

A stirred mixture of diethyl cis-1,2-cyclopropanedicarboxylate (53.0 g, 284.6 mmol) and sodium hydroxide (32.4 g, 809.1 mmol) in water (200 mL) was heated at reflux for 5 h. The mixture was then allowed to stir at room temperature overnight. The ethanol formed was evaporated under reduced pressure and the remaining aqueous solution was acidified with a slight excess of concentrated aqueous HCl (74.8 mL, 92.8 mmol). The mixture was evaporated to dryness under reduced pressure, and the residue was washed with hot ethyl acetate (3 times with 200 mL). The ethyl acetate layer was separated, dried (MgSO₄) and evaporated to dryness under reduced pressure to give 35.5 g of the title compound of Step B as a white solid (96% yield); m.p. 122°-124° C. IR (mineral oil, cm⁻¹), 1691.0 (C═O); 2600-3100, broad (OH).

Step C

preparation of cis-1,2-cyclopropanedicarboximide

A well-blended mixture of cis-1,2-cyclopropanedicarboxylic acid (5.0 g, 38.4 mmol) and urea (2.54 g, 42.24 mmol) in a round-bottom flask fitted with a condenser and magnetic stir bar, was immersed in a preheated oil bath (180° C.) and heated at 180° C. for 35 min with stirring. Gas evolution was observed during heating. The reaction mixture was then allowed to cool to room temperature. The mixture was then chromatographed on silica gel using 5% methanol in methylene chloride to obtain 2.4 g of the title compound of Step C as a white solid (56% yield); m.p. 93°-94° C.;

IR (mineral oil, cm⁻¹) 1678.9, 1758.3 (C═O).

Step D

Preparation of 3-azabicyclo 3.1.0!hexene hydrochloride salt

To a stirred solution of borane-tetrahydrofuran complex (1.0M, 35 mL, 135.0 mmol) under nitrogen and cooled to 0° C., was added cis-1,2-cyclopropanedicarboximide (5.0 g, 45.05 mmol) portionwise via solid addition funnel. The mixture was heated at reflux for 6 h. The reaction mixture was allowed to cool to 0° C., and then 6N aqueous HCl was added dropwise until the pH was approximately 3. The resultant mixture was stirred for an additional 1 h. The mixture was then made basic to pH 9 with 50% aqueous NaOH. Ethyl acetate (300 mL) and water (100 mL) were then added. The organic layer was separated and added to ethanol (100 mL). The solution was acidified to pH 6 with concentrated aqueous HCl and then evaporated to dryness under reduced pressure. The residue was triturated with cold 2-propanol. Evaporation of the 2-propanol under reduced pressure yielded 3.59 g of the title compound of Step D as a white solid (67% yield); m.p. 125°-127° C.

Step E

Preparation of (±)-3-azabicyclo 3.1.0!hexane-2-carboxylic acid

The compound, 3-azabicyclo 3.1.0!hexene hydrochloride salt (15.0 g, 125.43 mmol), was added to a saturated aqueous solution of potassium hydroxide (40 mL). The mixture was stirred at room temperature for 10 min and then washed with diethyl ether (3 times with 100 mL). The ether layer was dried (MgSO₄) and then added dropwise to a solution of N-chlorosuccinimide (29.7 g, 221.9 mmol) in diethyl ether (200 mL). The resultant mixture was stirred at ambient temperature for 3 h. Then, the mixture was filtered and the filtrate was washed with H₂ O (2 times with 50 mL), brine (50 mL) and dried (MgSO₄). The dried filtrate was added dropwise over a 30 min period to a solution of potassium hydroxide (8.28 g, 125.43 mmol) in absolute ethanol (300 mL). The resultant mixture was stirred at room temperature overnight. Filtration removed the inorganic salts, which were washed with ether. The combined filtrate and ether washings, which contained the imine, were treated with 13.05 g (125.4 mmol) of sodium bisulfite in 100 mL of water. After stirring vigorously for 15 min at room temperature, the two-phase mixture was treated with 6.48 g (125.43 mmol) of solid sodium cyanide. After stirring 2 h more at room temperature, the upper organic layer was decanted away and the aqueous layer was extracted with diethyl ether (2 times with 300 mL). The combined organic layer and ether extracts were dried (MgSO₄) and evaporated to dryness under reduced pressure to afford 12.1 g of 3-azabicyclo 3.1.0!hexane-2-carbonitrile. IR (neat, cm⁻¹): 2245.9 (CN). This crude product was used in the next reaction without further purification. A stirred solution of 12.1 g (112.0 mmol) of the crude carbonitrile and barium hydroxide hydrate (35.9 g, 114 mmol) in water (300 mL) was heated at reflux for 7 h. The reaction mixture was cooled to room temperature and acidified to pH 6 with concentrated sulfuric acid. The resulting white suspension was filtered through a CELITE (siliceous earth) bed, and the filtrate was allowed to settle for 30 min. The clear solution was decanted and evaporated under reduced pressure to dryness to give 9.8 g of the title compound of Step E as a white solid (69% yield). m.p. 211°-213° C.; IR (mineral oil, cm⁻¹): 1629.5 (C═O), 2600-3200 broad (OH).

Step F

Preparation of N- 4-chloro-2-fluoro-5-(2-propynyloxy)phenyl!-3-azabicyclo- 3.1.0!hexane-2-carboxamide

To a mixture of 2.36 g (11.79 mmol) of 4-chloro-2-fluoro-5-(2-propynyl)oxyaniline and 1.5 g (11.79 mmol) of (±)-3-azabicyclo 3.1.0!hexane-2-carboxylic acid in methylene chloride (150 mL) stirred under nitrogen and cooled to 5° C. was added trimethylaluminum dropwise (2.0M, 11.8 mL, 23.58 mmol). The resultant mixture was stirred at room temperature for 48 h. Water (100 mL) was added dropwise at ice-bath temperature. The solid inorganic material which formed was filtered, and the filtrate was dried (MgSO₄) and evaporated under reduced pressure to dryness. Flash chromatography on silica gel yielded 1.3 g of the product of Step F as a tan solid; m.p. 113°-115° C. IR (mineral oil, cm⁻¹): 1687.1 (C═O); 2123.5 (C.tbd.C).

Step G

Preparation of (±)-2- 4-chloro-2-fluoro-5-(2-propynyloxy)phenyl!tetrahydrocyclopropa 3.4!pyrrolo 1,2-c!imidazole-1,3(2H,3aH)-dione

Triphosgene (256 mg, 0.86 mmol) in 10 mL of dioxane was added dropwise at 0° C. to a stirred mixture of 80 mg, (2.59 mmol) of the product of Step F and triethylamine (1.8 mL, 12.95 mmol). The mixture was stirred at room temperature for 30 min. Evaporation of the mixture under reduced pressure gave a dry residue. Flash chromatography of the residue on silica gel gave 0.4 g of the title compound of Step G, a compound of the invention; m.p. 52°-54° C.; IR (mineral oil, cm⁻¹): 1784, 1722 (C═O); 2120 (C.tbd.C); ¹ H NMR: δ0.60-0.64 (m,1H), 1.20-1.31 (m,1H), 2.00-2.09 (m,1H), 2.10-2.20 (m,1H), 2.60 (s,1H), 3.11-3.19 (dd,1H), 4.18-4.23 (m,2H), 4.76-4.77 (d,2H), 7.02-7.06 (d,1H), 7.29-7.32 (d,1H).

EXAMPLE 2 Preparation of Ethyl 3- 2-chloro-4-fluoro-5-(hexahydro-1,3-dioxocyclopropa 3,4!pyrrolo 1,2-c!imidazol-2(3H)-yl)phenyl!-2-propenoate

Step A

Preparation of 2-chloro-4-fluoro-5-nitrobenzoic acid

A blend of 70% nitric acid (64.5 gm) and concentrated sulfuric acid (65 mL) was added dropwise over an hour period to a suspension of 2-chloro-4-fluoro-benzoic acid (125.0 gm, 716 mL). The white suspension was stirred mechanically for 30 minutes at ambient temperature. The thick white suspension was carefully poured into ice-water (100 mL). Ethyl acetate (800 mL) was added. The organic layer was separated, dried (MgSO₄) and evaporated to dryness under vacuum to give the title compound of Step A as a white solid (156.0 gm, 99%); m.p. 134°-136° C.; IR (cm⁻¹), C═O (1719.8). This intermediate was used without further purification.

Step B

Preparation of 2-chloro-4-fluoro-5-nitrobenzenemethanol

To a stirred solution of compound in Step A, Example 2 (120.0 gm, 546.45 mmol, in THF (400 mL), under N₂, at room temperature was slowly added Borane--THF complex 1.0M (726.8 mL, 726.8 mmol, Aldrich) over a 2-hour period (ice-bath used to keep temperature at 20°-25° C.). The resultant solution was stirred at room temperature for 3 hours followed by the solution being heated to reflux for 1 hour. H₂ O (30 mL) was added very slowly dropwise at 5° C. (ice-bath). The solution turned dark and H₂ O (1 L) and ethyl acetate (1 L) were added. The light yellow organic layer was separated, dried (MgSO₄) and evaporated to dryness under vacuum. The residue was chromatographed on silica gel using 20% ethyl acetate in hexane. The desired fractions were combined and evaporated under vacuum to obtain the title compound of Step B as a soft-yellow solid (91.3 gm, 81%); m.p. 39°-41° C., IR (nujol, cm⁻¹): 3321.2 (OH);

¹ H NMR δ: 2.18-2.22 (t,1H), 4.81-4.83 (d,2H), 7.34-7.36 (d,1H), 8.30-8.33 (d,1H).

Step C

Preparation of 2-chloro-4-fluoro-5-nitrobenzaldehyde

To a suspension of pyridinium chlorochromate (PCC) (48.46 gm, 224.0 mmol, Aldrich) under N₂, at room temperature, was rapidly added a solution of the compound of Step B, Example 2, (30.82 gm, 1.49.9 mmol) in methylene chloride (100 mL). The mixture turned dark and slowly became homogeneous. The dark mixture was stirred at room temperature for 3.5 hours.

The mixture was added to diethyl ether (800 mL) and filtered through FLORISIL (activated magnesium silicate). The remaining black residue was washed with Et₂ O (2×200 mL) and filtered through FLORISIL (activated magnesium silicate). The diethyl ether portions were combined, dried over magnesium sulfate and evaporated to dryness. The dry residue was chromatographed on silica gel using 10% ethyl acetate in hexane. Fractions of desired product were combined and evaporated under vacuum to give the title compound of Step C (20.2 gm, 66%) as a yellow oil. IR (neat, cm⁻¹): 1703.3 (C═O); ¹ H NMR δ: 7.47-7.51 (d,1H), 8.65-8.68 (d,1H), 10.41 (s,1H).

Step D

Preparation of Ethyl 3-(2-chloro-4-fluoro-5-nitrophenyl)-2-propenoate

A stirred mixture of the compound of Step C, Example 2, (11.5 gm, 56.51 mmol), (carbethoxymethyl)triphenylphosphonium bromide (24.2 gm, 56.51 mmol) and triethylamine (50 mL) in benzene (200 mL), under N₂, was heated to reflux for 1 hour. Water (200 mL) and ethyl acetate (200 mL) were added. The organic layer was separated, dried over magnesium sulfate and evaporated under reduce pressure to dryness. The residue was chromatographed on silica gel using hexane:EtOAc (15:5) mixture as eluent. The fractions were combined and evaporated under reduce pressure to obtain the title compound of Step D (9.3 gm, 60%) as a yellow solid; m.p. 86°-88° C.,

IR (nujol, cm⁻¹): 1716.8 (C═O); ¹ H NMR δ: 1.33-1.38 (t,3H), 4.29-4.31 (q,2H), 6.44-6.54 (d,1H), 7.40-7.44 (d,1H), 7.93-7.99 (d,1H), 8.34-8.38 (d,1H).

Step E

Preparation of Ethyl 3-(5-amino-2-chloro-4-fluoro-2-propenoate

A stirred solution of the compound of Step D, Example 2, (3.5 gm, 12.8 mmol) in acetic acid (30 mL) was heated to reflux under N₂. The heat source was removed and iron powder (2.2 gm) was added portionwise. The dark mixture was heated to reflux for 10 minutes and a thick precipitate formed. Water (100 mL) and ethyl acetate (100 mL) were added. The organic layer was separated, dried over magnesium sulfate, filtered through 0.5 cm of silica gel and evaporated to dryness under vacuum. The residue was chromatographed on silica gel using 10% ethyl acetate in hexane. Fractions containing the desired compound were combined and evaporated under reduce pressure to yield the title compound of Step E as a yellow solid (2.79 gm, 89%); m.p. 123°-124° C.; IR (nujol, cm⁻¹): 1704 (C═O), 3212 and 3388 (NH₂); ¹ H NMR δ: 1.31-1.36 (t,3H), 3.79 (broad s,2H), 4.26-4.28 (q,2H), 6.26-6.31 (d,1H), 6.99-7.02 (d,1H), 7.05-7.08 (d,1 H), 7.93-7.99 (d,1H).

Step F

Preparation of Phenylmethyl 2- 4-chloro-5-(3-ethoxy-3-oxo-1-propenyl)-2-fluorophenyl!amine!carbonyl!-3-azabicyclo 3.1.0!hexane-3-carboxylate

A mixture of the compound of Step D, Example 2, (2.7 gm, 11.09 mmol), carbobenzoyloxy (CBZ) protected (±)-3-azabicyclo 3.1.0!hexane-2-carboxylic acid (3.76 gm, 14.41 mmol), DCC (2.97 gm, 14.41 mmol), and 4-dimethylaminopyridine DMAP (39 mg, 1.4 mmol) in methylene chloride (100 mL) was stirred at room temperature for 24 hours. The mixture was filtered and the filtrate was evaporated to dryness. The residue was chromatographed on silica gel using 25% of ethyl acetate in hexane as eluent. The combined desired fractions were evaporated under vacuum to yield the title compound of Step F as a white solid 1.52 gm, 63%; m.p. 58°-60° C. IR (nujol, cm⁻¹): 1710 (C═O); ¹ H NMR δ: 0.22-0.28 (m,1H), 0.75-0.89 (m,2H), 1.19-1.38 (m,5H), 3.43-3.79 (m,3H), 4.21-4.28 (m,2H), 5.01-5.13 (m,2H), 6.42-6.48 (d,1H), 7.18-7.37 (m,7H), 7.95-8.00 (d,1H).

Step G

Preparation of Ethyl 3- 5- (3-azabicyclo 3.1.0!hexan-2-yl)carbonyl!amino!-2-chloro-4-fluorophenyl!-2-propenoate

To a stirred solution of borontrifluoride etherate (2.27 mL, 2.62 gm, 18.5 mmol) and ethanethiol (4.1 mL, 3.44 gm, 55.5 mmol) under N₂, at room temperature was added dropwise a solution of the compound of Step F, Example 2, (900.0 mg, 1.85 mmol) in CH₂ Cl₂ (1 mL). The resultant solution was stirred at room temperature for 4 hours. Water (100 mL) and CH₂ Cl₂ (200 mL) were added and the mixture was basified to pH-10 with solution of sodium hydroxide. The organic layer was separated, dried over MgSO₄ and evaporated to dryness under reduced pressure. The residue was chromatographed on silica gel using hexane:EtOAc (7:3) as eluent to give the title compound of step G as a white semi-solid 313 mg, 48%. IR (nujol, cm⁻¹): 1671.3 and 1723.0 (C═O) and 3364.4 (NH); ¹ H NMR δ: 0.05-0.07 (q,1H), 0.70-85 (m,1H), 1.31-1.36 (t,3H), 2.02-2.09 (m,2H), 3.01-3.08 (broad s,2H), 3.72-3.76 (s,1H), 4.08-4.18 (q,1H), 4.25-4.28 (m,2H), 6.45-6.52 (d,1H), 7.18-7.20 (d,1H), 7.97-8.02 (d,1H), 8.82-8.85 (d,1H), 9.98 (s,1H).

Step H

Preparation of Ethyl 3- 2-chloro-4-fluoro-5-(hexahydro-1,3-dioxocyclopropa 3,4!-pyrrolo 1,2-c!imidazol-2(3H)-yl!phenyl!-2-propenoate

To a stirred solution of the compound of Step G, Example 2, (300.0 mg, 0.85 mmol) and triethylamine (1.18 mL, 8.5 mmol) in CH₂ Cl₂ (50 mL), under N₂, at room temperature, was added dropwise a solution of triphosgene (84.0 mg, 0.28 mmol) in CH₂ Cl₂ (10 mL) over a period of 15 minutes. The solution was stirred at room temperature for 10 minutes. A mixture of CH₂ Cl₂ (100 mL) and H₂ O (50 mL) was added. The organic layer was separated, dried over MgSO₄ and concentrated under reduced pressure to dryness. The residue was chromatographed on silica gel using 25% ethyl acetate in hexane as eluent. Fractions containing the title compound were combined and evaporated under reduce pressure to yield the title compound, a compound of the invention, as a white solid (84.0 mg), 26%; m.p. 154°-156° C., IR (nujol, cm⁻¹): 1720.4 (C═O); ¹ H NMR δ: 0.61-0.63 (q,1H), 1.32-1.36 (m,4H), 2.01-2.03 (m,1H), 2.11-2.18 (m,1H), 3.12-3.18 (d,1H), 4.18-4.28 (m,4H), 6.37-6.41 (d,1H), 7.32-7.35 (d,1H), 7.59-7.62 (d,1H), 7.94-7.99 (d,1H).

EXAMPLE 3 Preparation of 2- 7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl!tetrahydrocyclopropa- 3,4!pyrrolo 1,2-c!imidazole-1,3(2H,5H)-dione

Step A

Preparation of Ethyl (5-fluoro-2-nitrophenoxy)acetate

A stirred mixture of 5-fluoro-2-nitrophenol (100.0 gm, 0.64 mol), ethyl bromoacetate (77.6 mL, 116.9 gm, 0.78 mol) and K₂ CO₃ (175.9 gm, 1.27 mol) in acetonitrile (800 mL), under N₂, was heated to reflux for 1 hour. The reaction mixture was filtered and the filtrate was washed with brine (200 mL), dried (MgSO₄) and evaporated to dryness to give the title compound of Step A, Example 3, as an orange solid (150.0 gm), 97%; m.p. 37°-39° C.; ¹ H NMR δ: 1.28-1.32 (t,3H), 4.23-4.29 (m,2H), 4.77 (s,2H), 6.64-6.68 (d,1H), 6.79-6.83 (t,1H), 7.96-8.01 (q,1H).

Step B

Preparation of 7-fluoro-2H-1,4-benzoxazin-3(4H)-one

To a solution of the compound of Step A, Example 3, (50.0 gm) in THF (100 mL), under N₂, was carefully added 10% Palladium on carbon (catalytic amount). The reaction vessel was pressurized with H₂ (45 psi) and shaken on a Parr hydrogenator for 4 hours. The reaction mixture was filtered through a CELITE (siliceous earth ) bed and the filtrate was evaporated to dryness under vacuum. The residue was triturated with Et₂ O to obtain the title compound of Step B as a white solid (32.0 gm), 93%; m.p. 200°-202° C.; ¹ H NMR δ: 4.58 (s,2H), 6.79-6.90 (m,3H), 10.72 (s,1H).

Step C

Preparation of 7-fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one

To a stirred solution of the compound of Step B, Example 3, (48.9 gm, 292.8 mmol) and concentrated H₂ SO₄ (100 mL), under N₂, was added a 26 mL mixture of HNO₃ (69-71%) and concentrated H₂ SO₄ dropwise at 25°-35° C. (ice-bath). The resultant solution was stirred at room temperature for 10 minutes. 400 mL of ice water was added portionwise to the solution at 0° C. (ice-bath) followed by the addition of EtOAc (1.5 L). The organic layer was separated, dried (MgSO₄) and evaporated to dryness to give the title compound of Step C as a tan solid (60.0 gm), 96%; m.p. 200°-202° C.; IR (nujol, cm⁻¹): 1703.5 (C═O); ¹ H NMR δ: 4.79 (s,2H), 7.26-7.29 (d,1H), 7.63-7.64 (d,1H), 11.05 (s,1H).

Step D

Preparation of 7-fluoro-6-nitro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one

To a stirred solution of the compound of Step C, Example 3, (4.0 gm, 18.86 mmol) in DMF (100 mL), under N₂, at 5° C. (ice-bath) was added sodium hydride (60% in mineral oil, 753.0 mg, 18.86 mmol) portionwise. When gas evolution stopped, propargyl bromide (80%, 2.24 gm, 18.86 mmol) was added dropwise. The dark solution was stirred at room temperature for 17 hours. The reaction was carefully poured into water (150 mL) and EtOAc (600 mL) was added. The organic layer was separated and evaporated to dryness. The residue was chromatographed on silica gel using 25% of ethyl acetate in hexane as eluent. Fractions of compound of interest were combined and evaporated to dryness to yield the title compound of Step D, Example 3, as a yellow solid (2.7 gm), 57%; m.p. 105°-107° C.; IR (nujol, cm⁻¹): 1695.3 (C═O) and 2120.6 (C.tbd.C); ¹ H NMR δ: 4.76-4.81 (m,4H), 6.91-6.94 (d,1H), 7.97-7.98 (d,1H), 2.35 (s,1H).

Step E

Preparation of 6-amino-7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one

Iron powder (6.0 gm, 107.9 mmol) was added portionwise over a 1.5 hour period under N₂, at room temperature, to a stirred solution of the compound of Step D, Example 3, (2.7 gm, 10.8 mmol) in methanol (100 mL). NaOAc (1.67 gm) was added and the mixture was filtered. The filtrate was basified to pH 9 using 50% NaOH. The mixture was filtered and the filtrate was evaporated to dryness. Flash chromatography yielded the title compound as a tan solid (300 mg), 13%; m.p. 132°-134° C.; IR (nujol, cm⁻¹): 3342 and 3287.8 (NH₂) and 2100 (C.tbd.C).

Step F

Preparation of phenylmethyl 2- 7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl!amino!carbonyl!-1-pyrrolidinecarboxylate

A mixture of the compound of Step E, Example 3, (1.3 gm), CBZ protected (±)-3-azabicyclo 3.1.0!hexane-2-carboxylic acid (2.3 gm), DCC (1.8 gm), DMAP (2.6 mg) in CH₂ Cl₂ (75 mL) was stirred at room temperature for 3 days. The reaction mixture was filtered and the filtrate was evaporated to dryness. Flash chromatography yielded the title compound of Step F as a white solid (1.41 gm), 51%; m.p. 72°-74° C.; IR (nujol, cm⁻¹): 1691 (C═O) and 3285.9 (NH); ¹ H NMR δ: 0.21-0.25 (m,1H), 0.83-0.85 (m,1H), 1.62-1.68 (m,2H), 2.01-2.04 (m,1H), 3.50-3.54 (m,1H), 3.75-3.79 (d,1H), 4.57-4.68 (m,3H), 5.07-5.09 (m,2H), 6.68-7.02 (d,1H), 7.26-7.36 (m,7H), 8.30-8.32 (d,1H) 8.82-8.84 (s,1H).

Step G

Preparation of N- 7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl!-3-azabicyclo 3.1.0!hexane-2-carboxamide

To a solution of boron trifluoride etherate (1.57 gm, 10.8 mmol) and ethanethiol (2.31 mL, 1.94 gm, 32.32 mmol) under N₂, at room temperature was added dropwise a solution of the compound of Step F, Example 3, (500.0 mg) in CH₂ Cl₂ (1 mL). The resultant clear solution was stirred at room temperature for 48 hours and the reaction was scrubbed with a bleach/50% NaOH/H₂ O-20%. 30 mL of water was added dropwise at room temperature followed by CH₂ Cl₂ (30 mL). The aqueous layer was separated and basified to pH 10 using 50% NaOH. Additional 30 mL of CH₂ Cl₂ was added and the organic layer was separated, dried (MgSO₄) and evaporated to dryness to give the title compound of Step G as a white solid (200 mg), 57%; m.p. 196°-198° C.; IR (nujol, cm⁻¹): 1676.0 (C═O), 3357.7 and 3301.7 (NH); ¹ H NMR δ: 0.08-0.09 (m,1H), 0.71-0.77 (m,1H), 1.41-1.43 (m,1H), 2.01-2.08 (m,1H), 2.11-2.17 (broad s, 1H), 2.31-2.32 (m,1H), 3.02 (s,2H), 3.72 (s,1H), 4.61 (s,2H), 4.75-4.81 (dd,2H), 6.79-6.81 (d,1H), 8.44-8.46 (d,1H), 9.85 (broad s,1H).

Step H

Preparation of 2- 7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl!tetrahydrocyclopropa 3,4!-pyrrolo 1,2-c!imidazole-1,3(2H,5H)-dione

A solution of triphosgene (57 mg) in CH₂ Cl₂ (1 mL) was added dropwise to a stirred solution of triethylamine (0.2 mL) and the compound of Step G, Example 3, (190 mg) in CH₂ Cl₂ (50 mL) under N₂ at room temperature. The solution was stirred at room temperature for 20 minutes. 30 mL of water was added. The organic layer was separated, dried (MgSO₄) and evaporated to dryness. Flash chromatography yielded the title compound of Step H, a compound of the invention, as a white solid (127 mg), 62%; m.p. 217°-219° C.; IR (nujol, cm⁻¹): 3253.6 and 2129.3 (C.tbd.C), 1625 and 1715 (C═O).

¹ H NMR δ: 0.61-0.64 (m,1H), 1.22-1.31 (m,1H), 2.01-2.11 (m,1H), 2.17-2.22 (m,1H), 2.25 (s,1H), 3.12-3.17 (dd,1H), 4.17-4.18 (m,2H), 4.67-4.68 (s,4H), 6.84-6.93 (d,1H), 7.11-7.14 (d,1H).

EXAMPLE 4 Preparation of Methyl 2-chloro-4-fluoro-5-(hexahydro-1,3-dioxocyclopropa 3,4!pyrrolo 1,2-c!imidazol-2(3H)-yl!benzoate

Step A

Preparation of 5-amino-2-chloro-4-fluorobenzoic acid

A solution of the compound of Step A in Example 2 (25.0 gm) in acetic acid (100 mL), under N₂, was heated to reflux. The heat source was removed and iron powder (6.38 gm) was added portionwise. The resultant mixture was stirred at ambient temperature for 15 minutes. 200 mL of water was added followed by addition of 500 mL of ethyl acetate. The organic layer was separated, washed with brine (3×50 mL), dried over magnesium sulfate and evaporated to dryness to yield the title compound as a tan solid (14.4 gm), 67%; m.p. 105°-107° C.; IR (nujol, cm⁻¹): 3396.9 and 3491.8 (NH₂) and 1702.0 (C═O).

Step B

Preparation of Methyl 5-amino-2-chloro-4-fluorobenzoate

Thionyl chloride (18.09 gm) was added dropwise to a solution of the compound of Step A of Example 4 (10.0 gm) in methanol (100 mL) under N₂ at 0° C. (ice-bath). The ice-bath was removed and the solution was heated to reflux for 2 hours. The solution was cooled to room temperature and then poured slowly into water (300 mL). The aqueous solution was extracted with 500 mL ethyl acetate. The organic layer was separated and dried over magnesium sulfate. Evaporation to dryness followed by flash chromatography yielded the title compound as a tan solid (4.3 gm), 40%; m.p. 76°-78° C.;

IR (nujol, cm⁻¹): 3404.1, 3324.5, and 1706.1; ¹ H NMR δ: 3.87-3.91 (m,5H), 7.07-7.11 (d,1H), 7.29-7.33 (d,1H).

Step C

Preparation of Phenylmethyl 2- 4-chloro-2-fluoro-5-(methoxycarbonyl)phenyl!amino!-carbonyl!-3-azabicyclo- 3.1.0!hexane-3-carboxylate

A solution of DCC (5.4 gm), DMAP (320 mg), CBZ protected (±)-3-azabicyclo 3.1.0!hexane-2-carboxylic acid (6.8 gm) and the compound of Step B of Example 4 (4.1 gm) in CH₂ Cl₂ (150 mL), under N₂, was stirred at room temperature for 17 hours. The reaction mixture was filtered and the filtrate was evaporated to dryness. Flash chromatography yielded the title compound as a sticky white solid (4.8 gm), 53%; m.p. (semi-solid); IR (nujol, cm⁻¹): 1708.6 and 3284.9; ¹ H NMR δ: 1.21-1.24 (m,1H), 0.72-0.89 (m,2H), 0.91-0.99 (t,3H), 1.21-1.37 (m,4H), 1.41-1.48 (m,2H), 1.66-1.71 (m,4H), 3.51-3.77 (m,2H), 4.31-4.37 (m,2H), 4.99-5.14 (m,2H), 7.24-7.39 (m,7H).

Step D

Preparation of Methyl 2-chloro-4-fluoro-5- 2-pyrrolidinylcarbonyl)amino!benzoate

To a solution of the compound of Step C of Example 4 (4.8 gm) in THF (100 mL), under N₂, was carefully added 10% Palladium on carbon (catalytic amount). The reaction mixture was pressurized with H₂ (45 psi) and shaken on a Paar hydrogenator for 2 hours. The mixture was filtered through a CELITE (siliceous earth) bed and the filtrate was evaporated to dryness. Flash chromatography yielded the title compound as a white solid (2.38 gm), 71%; m.p. 151°-153° C.

Step E

Preparation of Methyl 2-chloro-4-fluoro-5-(hexahydro-1,3-dioxocyclopropa 3,4!pyrrolo 1,2-c!Imidazol-2(3H)-yl)benzoate

A solution of triphosgene (135 mg) in CH₂ Cl₂ (2 mL) was added dropwise over a period of 10 minutes under N₂, at 0° C. (ice-bath) to a stirred solution of the compound of Step D of Example 4 (300 mg) in CH₂ Cl₂ (30 mL). The resultant mixture was stirred an additional 10 minutes at 0° C. (ice-bath). 50 mL of H₂ O was added and the aqueous mixture was extracted with CH₂ Cl₂ (100 mL). The organic layer was separated and dried over magnesium sulfate. The dried organic layer was evaporated under vacuum to dryness. The residue was chromatographed on silica gel using 25% of ethyl acetate in hexane as eluent. The fractions with the first eluting product were combined and evaporated under reduced pressure to yield the trans-isomer of the title compound, a compound of the invention, as a white solid (150 mg), 46%; m.p. 59°-62° C.; IR (nujol, cm⁻¹): 1726.9; ¹ H NMR δ: 0.61-0.68 (m,1H), 1.22-1.29 (m,1H), 2.01-2.04 (m,1H), 2.14-2.19 (m,1H), 3.17-3.18 (d,1H), 3.97 (s,3H), 4.18-4.21 (m,2H), 7.36-7.38 (d,1H), 7.92-7.95 (d,1H).

The fractions with the slower moving product were combined and evaporated under reduced pressure to yield the cis-isomer of the title compound, a compound of the invention, as a white solid (100 mg), 31%; m.p. 142°-143° C. ¹ H NMR (CDCl₃, 400 MHz): δ0.28-0.29 (m,1H), 0.87-0.89 (m,1H), 1.75-1.79 (m,1H), 1.93-1.95 (m,1H), 3.39-3.40 (dd,1H), 3.92 (s,3H), 3.95-3.98 (d,1H), 4.52-4.53 (d,1H), 7.35-7.37 (d,1H), 7.88-7.90 (d,1H).

EXAMPLE 5 Preparation of 3- 4-chloro-2-fluoro-5-(2-propynyloxy)phenyl!-amino!carbonyl!-3-azabicyclo 3.1.0!hexane-2-carboxylic acid

Step A

Preparation of 1-chloro-5-fluoro-4-isocyanato-2-(2-propynyloxy)benzene

To a stirred solution of 4-chloro-2 fluoro-5- (2-propynyl)oxy!-aniline (5.0 gm) and triethylamine (5.1 gm) in CH₂ Cl₂ (100 mL) under N₂, at 10° C. (ice-bath) was added triphosgene portionwise. The solution was heated to reflux for 5 hours. The solution was evaporated under vacuum and suspended in Et₂ O (200 mL). The suspension was filtered and the filtrate evaporated to dryness to give the title compound as a white solid (4.68 gm), 83%; IR (nujol, cm⁻¹): 3295 (C.tbd.C) and 2257 (N═C═O). This crude product was used as such in the next reaction.

Step B

Preparation of 3- 4-chloro-2-fluoro-5-(2-propynyloxy)phenyl!amino!carbonyl!-3-azabicyclo 3.1.0!hexane-2-carboxylic acid

A solution of the compound of Step A in Example 5 (3.0 gm) and the compound of Step E in Example 1 (1.69 gm) in CH₂ Cl₂ (100 mL), under N₂, was stirred at room temperature for 17 hours. The solution was evaporated to dryness. Flash chromatography yielded the title compound, a compound of the invention, as a white solid (1.2 g), 28%; m.p. 165°-170° C.; IR (nujol, cm⁻¹): 2127 (C.tbd.C), 1647 (C═O), 3293 and 3499.

The following Tables illustrate the compounds of the invention that are produced by the processes of the invention.

The following abbreviations are used in the Tables which follow. All alkyl groups are the normal isomers unless indicated otherwise.

    ______________________________________                                         n = normal                                                                               Et = ethyl   i = iso Pr = propyl                                     ______________________________________                                    

                  TABLE 1                                                          ______________________________________                                          ##STR19##                                                                     R.sup.1                                                                             R.sup.2                                                                               R.sup.3                                                                               R.sup.4           R.sup.5                                                                             V                                    ______________________________________                                         H    H      Cl     OCH(CH.sub.3).sub.2                                                                              Cl   O                                    H    H      Cl                                                                                     ##STR20##        Cl   O                                    H    H      F      OCH(CH.sub.3).sub.2                                                                              Cl   O                                    H    H      F      OCH.sub.2 CCH     Cl   O                                    H    H      Cl     OCH.sub.2 CCH     Cl   O                                    H    H      F      H                 Cl   O                                    H    H      F      OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                                            Cl   O                                    H    H      F      OCH(CH.sub.3)(CCH)                                                                               Cl   O                                    H    H      F      OCH.sub.2 C.sub.6 H.sub.5                                                                        Cl   O                                    H    H      F      OCH.sub.2 C.sub.6 H.sub.4 -4-CF.sub.3                                                            Cl   O                                    H    H      F      OCH.sub.2 C.sub.6 H.sub.4 -2-Cl                                                                  Cl   O                                    H    H      F      OCH.sub.2 C.sub.6 H.sub.4 -3-Cl                                                                  Cl   O                                    H    H      F      OCH(CCH)(CH(CH.sub.3).sub.2)                                                                     Cl   O                                    H    H      F      OC(CH.sub.3)(CCH)(CH.sub.2 CH.sub.3)                                                             Cl   O                                    H    H      F      OCH(CCH)(CH.sub.2).sub.4 CH.sub.3                                                                Cl   O                                    H    H      F      OCH(CCH)(CH.sub.2 CH.sub.3)                                                                      Cl   O                                    H    H      F      OCH.sub.2 CCCH.sub.3                                                                             Cl   O                                    H    H      F      OCH.sub.2 CH.sub.2 CCH                                                                           Cl   O                                    H    H      F      OCH(CH.sub.3)(CH.sub.2 CCH)                                                                      Cl   O                                    H    H      F      OCH(CH.sub.2 CH.sub.3)(CH.sub.2 CCH)                                                             Cl   O                                    H    H      F      OCH(CO.sub.2 CH.sub.2 CH.sub.3)(CH.sub.2).sub.4                                CH.sub.3          Cl   O                                    H    H      F      OP(O)(OCH.sub.2 CH.sub.3).sub.2                                                                  Cl   O                                    H    H      F      OCH.sub.2 CCH     Cl   S                                    H    F      F      OCH.sub.2 CCH     Cl   O                                    F    F      F      SCH.sub.2 CO.sub.2 Me                                                                            Cl   O                                    H    H      F      CO.sub.2 CH.sub.3 Cl   O                                    H    H      F                                                                                      ##STR21##        Cl   O                                    H    H      F      CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                     Cl   O                                    H    H      F      CHC(CH.sub.3)(CO.sub.2 Et)                                                                       Cl   O                                    H    H      F      CHCHCO.sub.2 Et   Cl   O                                    H    H      F      CHO               Cl   O                                    H    H      F      CHCHCO.sub.2 Me   Cl   O                                    H    H      F      CH.sub.2 CHCHCO.sub.2 Et                                                                         Cl   O                                    H    H      F      SCH(CO.sub.2 Et)(C.sub.5 H.sub.11)                                                               Cl   O                                    H    F      F      Cl                OMe  S                                    H    F      F      OCHMe.sub.2       OMe  O                                    F    F      Cl     H                 Br   O                                    H    H      F      OCH.sub.2 C(O)NHMe                                                                               Cl   S                                    H    H      F      SO.sub.2 Me       Cl   O                                    H    CH.sub.3                                                                              F      SCH.sub.2 CCH     Cl   O                                    H    H      F      OCF.sub.2 CHCF.sub.2                                                                             Cl   O                                    H    H      F      OCH.sub.2 CF.sub.3                                                                               Cl   O                                    ______________________________________                                    

                  TABLE 2                                                          ______________________________________                                          ##STR22##                                                                     R.sup.1                                                                               R.sup.2                                                                               R.sup.3                                                                               R.sup.7                                                                              R.sup.8       V                                     ______________________________________                                         H      H      F      H     CH.sub.2 CH.sub.3                                                                            O                                     H      H      F      H                                                                                     ##STR23##    O                                     H      H      F      H     CHFCO.sub.2 CH.sub.2 CH.sub.3                                                                O                                     H      H      F      H     CH.sub.2 CCH  O                                     H      H      F      H     CH.sub.2 CHCHCO.sub.2 CH.sub.2 CH.sub.3                                                      O                                     H      H      F      H     CH.sub.2 CCH  O                                     H      H      Cl     H     CH.sub.2 CCH  O                                     F      F      F      H     CH.sub.2 CCH  O                                     H      H      F      CH.sub.3                                                                             CH.sub.2 CCH  O                                     H      H      F      H     CH.sub.2 CO.sub.2 Et                                                                         O                                     ______________________________________                                    

                  TABLE 3                                                          ______________________________________                                          ##STR24##                                                                     R.sup.1                                                                               R.sup.2 R.sup.3                                                                               R.sup.5                                                                              R.sup.6                                                                             R.sup.7                                                                              V     W                                 ______________________________________                                         H      H       F      Cl    H    H     O     O                                 H      H       F      Cl    H    Me    O     S                                 H      H       F      Cl    Me   Me    O     O                                 H      H       Cl     Cl    H    H     O     O                                 H      H       Cl     Cl    Me   Me    O     S                                 H      H       F      Cl    H    H     S     O                                 ______________________________________                                    

                  TABLE 4                                                          ______________________________________                                          ##STR25##                                                                     R.sup.1  R.sup.2 R.sup.3 R.sup.8  V     W                                      ______________________________________                                         H        H       F       H        O     O                                      H        H       F       Me       S     O                                      H        H       Cl      H        O     S                                      H        H       Cl      Me       S     O                                      H        H       F       CH(CH.sub.3).sub.2                                                                      O     S                                      ______________________________________                                    

                  TABLE 5                                                          ______________________________________                                          ##STR26##                                                                     R.sup.1                                                                            R.sup.2                                                                              R.sup.3                                                                              R.sup.4          R.sup.5                                                                            R.sup.23                                                                              V                                  ______________________________________                                         H   H     F     OCH.sub.2 CCH    Cl  H      O                                  H   H     F     OCH(CCH)(CH(CH.sub.3).sub.2)                                                                    Cl  H      O                                  H   H     F     OCH.sub.2 CCH    Cl  CH.sub.3                                                                              O                                  H   H     F     OCH(CCH)(CH(CH.sub.3).sub.2)                                                                    Cl  CH.sub.2 CH.sub.3                                                                     O                                  H   F     F     OCH.sub.2 C.sub.6 H.sub.5                                                                       Cl  CH.sub.3                                                                              O                                  H   H     F     OCH.sub.2 CCH    Br  H      O                                  F   H     F     OCH.sub.2 CH.sub.3                                                                              Br  H      O                                  H   H     Cl    OCH(CCH)CH.sub.2 CH.sub.3                                                                       Cl  H      O                                  F   H     Cl    OCH(CH.sub.3).sub.2                                                                             Br  CH.sub.3                                                                              S                                  ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                          ##STR27##                                                                     R.sup.1                                                                               R.sup.2 R.sup.3 R.sup.8     R.sup.23                                                                             V                                     ______________________________________                                         H      H       F       CH.sub.2 CCH                                                                               H     O                                     H      H       F       CH.sub.2 CCH                                                                               Me    S                                     H      H       F       CH.sub.2 CO.sub.2 CH.sub.3                                                                 H     O                                     H      H       Cl      CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                        Me    O                                     ______________________________________                                    

                  TABLE 7                                                          ______________________________________                                          ##STR28##                                                                     R.sup.1                                                                               R.sup.2                                                                               R.sup.3                                                                               R.sup.4       R.sup.5                                                                               X                                    ______________________________________                                         H      H      F      OCH.sub.2 CCH Cl     Cl                                   H      H      F      OCH(CH.sub.3).sub.2                                                                          Br     Cl                                   H      H      Cl     OCH(CCH)(Et)  Cl     Cl                                   H      H      F      OCH(CH.sub.3).sub.2                                                                          Cl     CN                                   H      H      F      OCH.sub.2 CH.sub.2 OCH.sub.3                                                                 OCH.sub.3                                                                             Cl                                   H      H      F      SCH.sub.2 CF.sub.3                                                                           Cl     Cl                                   H      H      F      OCH.sub.2 CF.sub.3                                                                           Cl     Cl                                   H      H      F      OCH.sub.2 C(O)NHMe                                                                           Cl     Cl                                   H      H      F      SO.sub.2 Me   Cl     Cl                                   H      H      F      OCH.sub.2 CH.sub.2 OCHF.sub.2                                                                Cl     Cl                                   H      H      F      SCH.sub.2 CCH Cl     Cl                                   ______________________________________                                    

                  TABLE 8                                                          ______________________________________                                          ##STR29##                                                                     R.sup.1                                                                               R.sup.2 R.sup.3 R.sup.5                                                                              R.sup.6                                                                               R.sup.7                                                                               X                                   ______________________________________                                         H      H       F       Cl    H      H      Cl                                  H      H       F       Cl    CH.sub.3                                                                              CH.sub.3                                                                              Cl                                  H      H       Cl      Cl    H      H      Cl                                  ______________________________________                                    

                  TABLE 9                                                          ______________________________________                                          ##STR30##                                                                     R.sup.1  R.sup.2 R.sup.3 R.sup.4       R.sup.5                                 ______________________________________                                         H        H       F       OCH.sub.2 CCH Cl                                      H        H       Cl      OCH.sub.2 CH(CH.sub.3).sub.2                                                                 Cl                                      H        H       F       OCH.sub.2 CH.sub.3                                                                           Cl                                      H        H       F       OCH.sub.2 CO.sub.2 Me                                                                        Cl                                      H        H       F       OC(O)N(CH.sub.3).sub.2                                                                       Cl                                      H        H       F       OC(O)NHCH.sub.3                                                                              Cl                                      H        H       Cl      OCH.sub.2 F   Cl                                      H        H       F                                                                                       ##STR31##    Cl                                      ______________________________________                                    

Formulation/Utility

The compounds of Formulae I-IV are useful as herbicides in agriculture. To carry out this utility, any of the compounds of Formulae I-IV can generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent and/or a surfactant wherein the formulation is consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated"). Encapsulation can control or delay release of the active ingredient. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.

The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.

    ______________________________________                                                       Weight Percent                                                                 Active                                                                         Ingredient                                                                             Diluent   Surfactant                                     ______________________________________                                         Water-Dispersible and                                                                          5-90      0-74      1-15                                       Water-soluble                                                                  Granules, Tablets and Powders.                                                 Suspensions, Emulsions,                                                                        5-50      40-95     0-15                                       Solutions                                                                      (including Emulsifiable                                                        Concentrates)                                                                  Dusts           1-25      70-99     0-5                                        Granules and Pellets                                                                           0.01-99     5-99.99 0-15                                       High Strength Compositions                                                                     90-99     0-10      0-2                                        ______________________________________                                    

Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J., as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.

Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltarates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillinite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. Pat. No. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, N.Y., 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701 and U.S. Pat. No. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et at., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989.

In the following Examples, all percentages are by weight and all formulations are worked up in conventional ways. Compound 23 refers to the compound listed in Index Table A hereinafter.

Example A

    ______________________________________                                         High Strength Concentrate                                                      ______________________________________                                         Compound 23         98.5%                                                      silica aerogel      0.5%                                                       synthetic amorphous fine silica                                                                    1.0%.                                                      ______________________________________                                    

Example B

    ______________________________________                                         Wettable Powder                                                                ______________________________________                                         Compound 23           65.0%                                                    dodecylphenol polyethylene glycol ether                                                              2.0%                                                     sodium ligninsulfonate                                                                               4.0%                                                     sodium silicoaluminate                                                                               6.0%                                                     montmorillonite (calcined)                                                                           23.0%.                                                   ______________________________________                                    

Example C

    ______________________________________                                         Granule                                                                        ______________________________________                                         Compound 23          10.0%                                                     attapulgite granules (low volatile                                                                  90.0%.                                                    matter, 0.71/0.30 mm; U.S.S. No.                                               25-50 sieves)                                                                  ______________________________________                                    

Example D

    ______________________________________                                         Extruded Pellet                                                                ______________________________________                                         Compound 23          25.0%                                                     anhydrous sodium sulfate                                                                            10.0%                                                     crude calcium ligninsulfonate                                                                       5.0%                                                      sodium alkylnaphthalenesulfonate                                                                    1.0%                                                      calcium/magnesium bentonite                                                                         59.0%.                                                    ______________________________________                                    

Tests results indicate that the compounds of Formulae I-IV are highly active preemergent and/or postemergent herbicides and/or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, around billboards and highway and railroad structures. Some of the compounds are useful for the control of selected grass and broadleaf weeds such as morningglory, cocklebur, velvetleaf, giant foxtail, barnyardgrass and lambsquarters, with tolerance to important agronomic crops which include but are not limited to barley, cotton, wheat, rape, sugarbeets, corn, soybeans, rice, and plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, conifers, e.g., loblolly pine, and turf species Kentucky bluegrass, St. Augustine grass, Kentucky rescue and bermudagrass. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.

Compounds of Formulae I-IV can be used alone or in combination with other commercial herbicides, insecticides or fungicides. A mixture of one or more of the following herbicides with a compound of Formula I can be particularly useful for weed control. Examples of other herbicides with which compounds of this invention can be formulated are: acetochlor, acifluorfen, acrolein, 2-propenal, alachlor, ametryn, amidosulfuron, ammonium sulfamate, amitrole, anilofos, asulam, atrazine, barban, benefin, bensulfuron methyl, bensulide, bentazon, benzofluor, benzoylprop, bifenox, bromacil, bromoxynil, bromoxynil heptanoate, bromoxynil octanoate, butachlor, buthidazole, butralin, butylate, cacodylic acid, 2-chloro-N,N-di-2-propenylacetamide, 2-chloroallyl diethyldithiocarbamate, chloramben, chlorbromuron, chloridazon, chlorimuron ethyl, chlormethoxynil, chlornitrofen, chloroxuron, chlorpropham, chlorsulfuron, chlortoluron, cinmethylin, cinosulfuron, clethodim, clomazone, cloproxydim, clopyralid, calcium salt of methylarsonic acid, cyanazine, cycloate, cycluron, cyperquat, cyprazine, cyprazole, cypromid, dalapon, dazomet, dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate, desmedipham, desmetryn, dicamba, dichlobenil, dichlorprop, diclofop, diethatyl, difenzoquat, diflufenican, dimepiperate, dinitramine, dinoseb, diphenamid, dipropetryn, diquat, diuron, 2-methyl-4,6-dinitrophenol, disodium salt of methylarsonic acid, dymron, endothall, S-ethyl dipropylcarbamothioate, esprocarb, ethalfluralin, ethametsulfuron methyl, ethofumesate, fenac, fenoxaprop, fenuron, salt of fenuron and trichloroacetic acid, flamprop, fluazifop, fluazifop-P, fluchloralin, flumesulam, flumipropyn, fluometuron, fluorochloridone, fluorodifen, fluoroglycofen, flupoxam, fluridone, fluroxypyr, fluzasulfuron, fomesafen, fosamine, glyphosate, haloxyfop, hexaflurate, hexazinone, imazamethabenz, imazapyr, imazaquin, imazamethabenz methyl, imazethapyr, imazosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, karbutilate, lactofen, lenacil, linuron, metobenzuron, metsulfuron methyl, methylarsonic acid, monoammonium salt of methylarsonic acid, (4-chloro-2-methylphenoxy)acetic acid, S,S"-dimethyl-2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinedicarbothioate, mecoprop, mefenacet, mefluidide, methalpropalin, methabenzthiazuron, metham, methazole, methoxuron, metolachlor, metribuzin, 1,2-dihydropyridazine-3,6-dione, molinate, monolinuron, monuron, monuron salt and trichloroacetic acid, monosodium salt of methylarsonic acid, napropamide, naptalam, neburon, nicosulfuron, nitralin, nitrofen, nitrofluorfen, norea, norflurazon, oryzalin, oxadiazon, oxyfluorfen, paraquat, pebulate, pendimethalin, perfluidone, phenmedipham, picloram, 5- 2-chloro-4-(trifluoromethyl)phenoxy!-2-nitroacetophenone oxime-O-acetic acid methyl ester, pretilachlor, primisulfuron, procyazine, profluralin, prometon, prometryn, pronamide, propachlor, propanil, propazine, propham, prosulfalin, prynachlor, pyrazolate, pyrazon, pyrazosulfuron ethyl, quinchlorac, quizalofop ethyl, rimsulfuron, secbumeton, sethoxydim, siduron, simazine, 1-(α,α-dimethylbenzyl)-3-(4-methylphenyl)urea, sulfometuron methyl, trichloroacetic acid, tebuthiuron, terbacil, terbuchlor, terbuthylazine, terbutol, terbutryn, thifensulfuron methyl, thiobencarb, tri-allate, trialkoxydim, triasulfuron, tribenuron methyl, triclopyr, tridiphane, trifluralin, trimeturon, (2,4-dichlorophenoxy)acetic acid, 4-(2,4-dichlorophenoxy)butanoic acid, vernolate, and xylachlor.

In certain instances, combinations with other herbicides having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management.

A herbicidally effective amount of the compounds of Formulae I-IV is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of a compound(s) of Formulae I-IV is applied at rates from about 0.01 to 20 kg/ha with a preferred rate range of 0.02 to 10 kg/ha. One skilled in the art can easily determine application rates necessary for the desired level of weed control.

The following Tests demonstrate the control efficacy of the compounds of Formulae I-IV against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables A-D for compound descriptions.

    ______________________________________                                         Index Table A                                                                   ##STR32##                                                                     Formula I wherein Q is Q-1                                                     Cmpd                                     m.p.                                  No.   R.sup.3                                                                              R.sup.4           R.sup.5                                                                            Stereo.sup.a                                                                          (°C.)                          ______________________________________                                         1     Cl    OCH(CH.sub.3).sub.2                                                                              Cl  trans  55-57                                 2     F     OCH.sub.2 CCH     C1  --     52-54                                 (Ex. 1)                                                                        3     F     OCH(CH.sub.3).sub.2                                                                              Cl  trans  oily                                                                           solid.sup.b                           4     F     CO.sub.2 CH.sub.3 C1  trans  59-62                                 (Ex. 4)                                                                        5     Cl    O-cyclopentyl     Cl  --     58-60                                 6     Cl    OCH.sub.2 CN      Cl  --     65-67                                 7     Cl    OCH.sub.2 CO.sub.2 CH.sub.3                                                                      C1  --     131-                                                                           133                                   8     Cl    OCH.sub.2 -cyclopropyl                                                                           Cl  --     61-63                                 9     F     H                 Cl  --     89-90                                 10    Cl    OCH.sub.2 CCH     Cl  --     50-52                                 11    F     SCH.sub.2 CO.sub.2 CH.sub.3                                                                      Cl  --     44-46                                 12    F     OP(O)(OCH.sub.2 CH.sub.3).sub.2                                                                  Cl  --     oil.sup.b                             13    F     OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                                            Cl  --     oil.sup.b                             14    F                                                                                     ##STR33##        Cl  --     89-91                                 15    F     CHC(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                          Cl  --     36-40                                 16    F     CO.sub.2 CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                     Cl  --     38-42                                 17    F     CH.sub.2 CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                     Cl  --     75-77                                 18    F     CHCHCO.sub.2 CH.sub.2 CH.sub.3                                                                   Cl  --     154-                                  (Ex. 2)                                  156                                   19    F     CHO               Cl  --     114-                                                                           116                                   20    F     CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                     Cl  --     oil.sup.b                             21    F     CO.sub.2 CH.sub.3 Cl  cis    142-                                  (Ex. 4)                                  143                                   22    F     O-cyclopentyl     Cl  --     100-                                                                           112                                   23    F     OCH(CH.sub.3)CCH  Cl  --     46-48                                 24    F     OCH.sub.2 -(4-CF.sub.3 --Ph)                                                                     Cl  --     147-                                                                           149                                   25    F     OCH.sub.2 -(3-ClPh)                                                                              Cl  --     197-                                                                           199                                   26    F     OCH.sub.2 -(2-ClPh)                                                                              Cl  --     152-                                                                           154                                   27    F     CHCHCO.sub.2 CH.sub.3                                                                            Cl  --     159-                                                                           161                                   28    F     OCH.sub.2 Ph      Cl  --     126-                                                                           128                                   29    F     OCH(CCH)CH(CH.sub.3).sub.2                                                                       Cl  trans/mix                                                                             60-62                                 30    F     OCH(CCH)CH(CH.sub.3).sub.2                                                                       Cl  cis/mix                                                                               61-63                                 31    F     OC(CH.sub.3)(CCH)CH.sub.2 CH.sub.3                                                               Cl  trans/mix                                                                             60-63                                 32    F     OC(CH.sub.3)(CCH)CH.sub.2 CH.sub.3                                                               Cl  cis/mix                                                                               oil.sup.b                             33    F     OCH(CCH)(CH.sub.2).sub.4 CH.sub.3                                                                Cl  trans/mix                                                                             oil.sup.b                             34    F     OCH(CCH)CH.sub.2 CH.sub.3                                                                        Cl  trans/mix                                                                             oil.sup.b                             35    F     OCH.sub.2 CCCH.sub.3                                                                             Cl  --     114-                                                                           116                                   36    F     OCH.sub.2 CH.sub.2 CCH                                                                           Cl  --     103-                                                                           105                                   37    F     OCH(CH.sub.3)CH.sub.2 CH                                                                         Cl  --     51-53                                 38    F     OCH(CH.sub.2 CH.sub.3)CH.sub.2 CCH                                                               Cl  --     oil.sup.b                             39    F     SCH (CH.sub.2).sub.4 CH.sub.3 !CO.sub.2 CH.sub.2 CH.sub.3                                        Cl  --     oil.sup.b                             40    F     OCH (CH.sub.2).sub.4 CH.sub.3 !CO.sub.2 CH.sub.2 CH.sub.3                                        Cl  --     oil.sup.b                             ______________________________________                                          .sup.a This column indicates the stereochemistry of the compound. "Trans"      and "Cis" is the relative orientation between the cyclopropyl ring and th      imidazolinedione ring. "Mix" indicates that the compound is a mixture of       diastereomers due to the remote chiral center on R.sup.4. A dash (--)          indicates that the relative stereochemistry was not determined or the          compound is a mixture of trans and cis. All compounds are racemic.             .sup.b See Index Table D for .sup.1 HNMR data.                           

    ______________________________________                                         Index Table B                                                                   ##STR34##                                                                     Formula I wherein in Q is Q-5                                                  Cmpd No.                                                                              R.sup.3                                                                              R.sup.7                                                                               R.sup.8       Stereo.sup.a                                                                         m.p. (°C.)                      ______________________________________                                         41     F     H      CH.sub.2 CH.sub.3                                                                            --    204-206                                42 (Ex. 3)                                                                            F     H      CH.sub.2 CCH  --    217-219                                43     F     H      CH.sub.2 -cyclopropyl                                                                        --    82-85                                  44     F     H      CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                         --    71-73                                  45     F     H      CHFCO.sub.2 CH.sub.2 CH.sub.3                                                                --    75-77                                  46     F     H      CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                          --    142-144                                47     F     CH.sub.3                                                                              CH.sub.2 CCH  --    155-157                                48     F     H      CH.sub.2 CHCHCO.sub.2 CH.sub.2 CH.sub.3                                                      --    180-182                                ______________________________________                                          .sup.a This column indicates the stereochemistry of the compound. "Trans"      and "Cis" is the relative orientation between the cyclopropyl ring and th      imidazolinedione ring. A dash (--) indicates that the relative                 stereochemistry was not determined or the compound is a mixture of trans       and cis. All compounds are racemic.                                      

                  Index Table C                                                    ______________________________________                                          ##STR35##                                                                     Formula III wherein Q is Q-1                                                   Cmpd                                                                           No.   R.sup.3                                                                              R.sup.4        R.sup.5                                                                            R.sup.23                                                                            Stereo.sup.a                                                                         m.p. (°C.)                    ______________________________________                                         49    F     OCH.sub.2 Ph   Cl  H    --    143-145                              50    F     OCH.sub.2 CCH  Cl  H    --    165-170                              (Ex. 5)                                                                        51    F     OCH(CCH)CH(CH.sub.3).sub.2                                                                    Cl  H    --    61-65                                52    F     OCH(CH.sub.3)CCH                                                                              Cl  H    --    157-159                              53    F     OCH.sub.2 CCH  Cl  CH.sub.3                                                                            --    110-112                              54    F     OCH(CH.sub.3)CCH                                                                              Cl  CH.sub.3                                                                            --    62-64                                ______________________________________                                          .sup.a This column indicates the stereochemistry of the compound. "Trans"      and "Cis" is the relative orientation between the cyclopropyl ring and th      CO.sub.2 R.sup.23 group. A dash (--) indicates that the relative               stereochemistry was not determined or the compound is a mixture of trans       and cis. All compounds are racemic.                                      

                                      Index Table D                                __________________________________________________________________________     Cmpd No.                                                                               .sup.1 H NMR Data (CDCl.sub.3 solution).sup.a                          __________________________________________________________________________     3       δ: 0.18 (m,1H), 0.82-0.85 (m,1H), 1.37-1.40 (d,6H),                      1.70-1.80                                                                      (m,1H), 1.90-1.99 (m,1H), 3.31-3.40 (dd,1H), 3.94-3.98 (d,1H),                 4.47-4.51 (m,2H), 6.79-6.82 (d,1H), 7.25-7.28 (d,1H).                  12      δ: 0.59-0.63 (q,1H), 1.19-1.23 (t,2H), 1.24-1.29 (m,1H),                 1.37-1.61                                                                      (m,5H), 2.12-2.18 (m,1H), 3.11-3.18 (d,1H), 3.47-3.49 (q,2H),                  4.21-4.32 (m,4H), 7.31-7.36 (d,1H), 7.52-7.59 (d,1H).                  13      δ: 0.59-0.62 (q,1H), 1.20-1.25 (m,4H), 2.00-2.08 (m,1H),                 2.10-2.20                                                                      (m,1H), 3.10-3.19 (dd,1H), 3.61-3.63 (q,2H), 3.80-3.84 (q,2H),                 4.15-4.18 (m,4H), 6.90-6.94 (d,1H), 7.29 (s,1H).                       20      δ: 0.49-0.69 (dq,1H), 0.97-0.99 (t,1H), 1.18-1.32 (m,3H),                1.21-1.32                                                                      (m,1H), 1.61-1.9 (m,4H), 2.08-2.19 (m,1H), 3.0-3.19 (dd,1H),                   3.80-3.90 (m,1H), 4.05-4.10 (m,1H), 4.30-4.38 (m,1H), 7.35-7.39                (d,1H), 7.90-7.92 (d,1H).                                              32      δ: 0.05-0.09 (m,1H), 1.80-1.88 (q,1H), 1.90-1.02 (m,1H),                 1.12-1.13                                                                      (t,3H), 1.56-1.59 (d,4H), 1.70-1.79 (m,1H), 1.85-2.02 (m,2H),                  3.32-3.39 (dd,1H), 3.94-3.99 (d,1H), 4.44-4.45 (d,1H), 7.24-7.27               (d,1H), 7.44-7.46 (d,1H).                                              33      δ: 0.60-0.65 (q,1H), 1.85-1.97 (m,3H), 1.35-1.36 (m,6H),                 1.95-2.02                                                                      (m,4H), 2.10-2.19 (m,1H), 2.55-2.56 (m,1H), 3.09-3.19 (d,1H),                  4.16 (s,1H), 4.19-4.22 (m,1H), 4.63-470 (t,1H), 7.08-7.12                      (t,1H),                                                                        7.27-7.29 (d,1H).                                                      34      δ: 1.59-1.65 (m,1H), 1.12-1.17 (t,3H), 1.22-1.32 (m,1H),                 2.03-2.05                                                                      (m,3H), 2.10-2.19 (m,1H), 3.10-3.19 (d,1H), 4.16 (s,1H), 4.18-                 4.23 (m,1H), 2.61-2.68 (t,1H), 7.08-7.11 (t,1H), 7.27-7.30                     (d,1H).                                                                38      δ: 0.61-0.64 (m,1H), 1.00-1.05 (m,3H), 1.24-1.33 (m,1H),                 1.81-1.97                                                                      (m,2H), 2.04-2.05 (m,2H), 2.11-2.19 (m,1H), 2.51-2.62 (m,2H),                  3.12-3.18 (d,1H), 4.16 (s,1H), 4.19-4.22 (m,1H), 4.27-4.30                     (t,1H),                                                                        6.92-6.98 (m,1H), 7.27-7.29 (d,1H).                                    39      δ: 0.59-0.62 (m,1H), 0.85-0.89 (m,3H), 1.13-1.18 (t,3H),                 1.30-1.33                                                                      (m,5H), 1.40-1.43 (m,1H), 3.10-3.19 (d,1H), 3.60-3.79 (m,2H),                  4.03-4.21 (m,4H), 7.30-7.36 (d,1H), 7.52-7.58 (d,1H).                  40      δ: 0.59-0.62 (m,1H), 0.85-0.92 (m,3H), 1.24-1.26 (m,4H),                 1.30-1.39                                                                      (m,4H), 1.45-1.58 (m,2H), 1.98-2.08 (m,3H), 2.11-2.18 (m,1H),                  3.08-3.18 (d,1H), 4.12-4.26 (m,4H), 4.55-4.61 (m,1H), 6.78-6.82                (m,1H), 7.22-7.24 (d,1H).                                              __________________________________________________________________________      .sup.a1 H NMR data are in ppm downfield from tetramethylsilane. Couplings      are designated by (s)singlet, (d)doublet, (t)triplet, (q)quartet,              (m)multiplet, (dd)doublet of doublets, (dq)doublet of quartets.          

TEST A

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), cheatgrass (Bromus secalinus), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which includes a surfactant. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.

                                      TABLE A                                      __________________________________________________________________________             COMPOUND                                                               Rate 1000 g/ha                                                                         41                                                                     __________________________________________________________________________     POSTEMERGENCE                                                                  Barley  10                                                                     Barnyardgrass                                                                          10                                                                     Bedstraw                                                                               10                                                                     Blackgrass                                                                             10                                                                     Cheatgrass                                                                             --                                                                     Chickweed                                                                              10                                                                     Cocklebur                                                                              10                                                                     Corn     9                                                                     Cotton  10                                                                     Crabgrass                                                                              10                                                                     Downy brome                                                                            10                                                                     Giant foxtail                                                                          10                                                                     Lambsquarter                                                                           10                                                                     Morningglory                                                                           10                                                                     Nutsedge                                                                               10                                                                     Rape    10                                                                     Rice    10                                                                     Sorghum 10                                                                     Soybean 10                                                                     Sugar beet                                                                             10                                                                     Velvetleaf                                                                             10                                                                     Wheat   10                                                                     Wild buckwheat                                                                         10                                                                     Wild oat                                                                               10                                                                     PREEMERGENCE                                                                   Barley  10                                                                     Barnyardgrass                                                                          10                                                                     Bedstraw                                                                               10                                                                     Blackgrass                                                                              9                                                                     Cheatgrass                                                                             --                                                                     Chickweed                                                                              10                                                                     Cocklebur                                                                              10                                                                     Corn    10                                                                     Cotton  10                                                                     Crabgrass                                                                              10                                                                     Downy brome                                                                            10                                                                     Giant foxtail                                                                          10                                                                     Lambsquarter                                                                           10                                                                     Morningglory                                                                           10                                                                     Nutsedge                                                                               10                                                                     Rape    10                                                                     Rice    10                                                                     Sorghum 10                                                                     Soybean 10                                                                     Sugar beet                                                                             10                                                                     Velvetleaf                                                                             10                                                                     Wheat   10                                                                     Wild buckwheat                                                                         10                                                                     Wild oat                                                                               10                                                                     __________________________________________________________________________                 COMPOUND                                                           Rate 400 g/ha                                                                              1  2           9  23                                               __________________________________________________________________________     POSTEMERGENCE                                                                  Barley      8  9           6  10                                               Barnyardgrass                                                                              10 10          9  10                                               Bedstraw    8  10          9  10                                               Blackgrass  6  10          3  9                                                Cheatgrass  -- --          -- --                                               Chickweed   6  10          4  9                                                Cocklebur   8  10          9  10                                               Corn        7  9           8  6                                                Cotton      10 10          10 10                                               Crabgrass   8  9           9  9                                                Downy brome 5  8           3  9                                                Giant foxtail                                                                              6  10          9  9                                                Lambsquarter                                                                               10 10          10 10                                               Morningglory                                                                               8  10          9  10                                               Nutsedge    5  6           6  6                                                Rape        6  10          10 10                                               Rice        7  10          9  9                                                Sorghum     6  9           7  10                                               Soybean     9  10          9  10                                               Sugar beet  10 10          10 10                                               Velvetleaf  10 10          10 10                                               Wheat       6  9           6  6                                                Wild buckwheat                                                                             10 10          10 10                                               Wild oat    8  10          6  9                                                PREEMERGENCE                                                                   Barley      1  7           5  8                                                Barnyardgrass                                                                              9  9           10 10                                               Bedstraw    10 10          2  10                                               Blackgrass  6  8           2  5                                                Cheatgrass  -- --          -- --                                               Chickweed   1  10          5  10                                               Cocklebur   6  10          4  3                                                Corn        7  9           5  6                                                Cotton      3  10          5  10                                               Crabgrass   9  10          9  10                                               Downy brome 3  10          8  9                                                Giant foxtail                                                                              10 10          9  10                                               Lambsquarter                                                                               10 10          10 10                                               Morningglory                                                                               8  10          9  10                                               Nutsedge    0  2           3  0                                                Rape        9  10          10 10                                               Rice        3  6           7  6                                                Sorghum     6  8           3  8                                                Soybean     9  10          9  10                                               Sugar beet  9  10          10 10                                               Velvetleaf  10 10          10 10                                               Wheat       2  6           4  4                                                Wild buckwheat                                                                             6  10          9  9                                                Wild oat    9  9           6  9                                                __________________________________________________________________________             COMPOUND                                                               Rate 200 g/ha                                                                          3 4 5 6 8 10                                                                               11                                                                               12                                                                               14                                                                               17                                                                               18                                                                               19                                                                               20                                                                               21                                                                               22                                                                               24                                                                               25                                     __________________________________________________________________________     POSTEMERGENCE                                                                  Barley  4 5 4 4 2 3 4 6 5 3 5 3 5 2 7 3 4                                      Barnyardgrass                                                                          4 9 5 2 4 9 9 6 8 6 10                                                                               2 6 2 7 2 2                                      Bedstraw                                                                               6 10                                                                               8 7 6 8 10                                                                               9 9 9 10                                                                               6 10                                                                               7 9 5 6                                      Blackgrass                                                                             3 5 3 3 3 5 4 5 5 3 4 2 3 2 3 3 4                                      Cheatgrass                                                                             --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               1 3 --                                                                               --                                                                               --                                                                               --                                     Chickweed                                                                              4 9 5 3 2 6 6 6 7 3 7 3 3 2 8 2 5                                      Cocklebur                                                                              3 9 7 6 7 8 10                                                                               8 9 10                                                                               10                                                                               8 8 5 9 9 8                                      Corn    2 6 4 3 2 4 8 2 4 6 8 7 3 2 3 2 2                                      Cotton  9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                     Crabgrass                                                                              6 6 3 3 3 7 5 2 4 4 8 6 5 2 2 2 3                                      Downy brome                                                                            4 5 4 4 3 4 5 5 3 4 5 --                                                                               --                                                                               2 4 2 3                                      Giant foxtail                                                                          4 7 4 3 4 8 7 4 5 4 5 4 6 2 3 2 3                                      Lambsquarter                                                                           8 9 10                                                                               8 9 10                                                                               9 9 9 9 9 8 7 5 9 9 9                                      Morningglory                                                                           4 10                                                                               8 9 9 8 10                                                                               9 9 9 10                                                                               7 8 8 10                                                                               6 9                                      Nutsedge                                                                               1 5 2 1 1 3 --                                                                               2 6 --                                                                               --                                                                               --                                                                               --                                                                               1 --                                                                               1 2                                      Rape    6 10                                                                               6 6 4 8 10                                                                               8 10                                                                               10                                                                               10                                                                               5 8 4 10                                                                               3 9                                      Rice    4 10                                                                               5 5 5 9 7 7 8 7 7 7 5 4 6 5 3                                      Sorghum 3 8 5 3 3 8 5 3 5 8 7 6 5 3 4 3 3                                      Soybean 6 8 8 6 8 8 5 9 7 6 9 9 9 6 7 7 5                                      Sugar beet                                                                             8 10                                                                               10                                                                               9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9 10                                                                               6 9 9 10                                                                               10                                                                               9                                      Velvetleaf                                                                             4 10                                                                               10                                                                               8 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9 10                                                                               9 10                                     Wheat   5 6 4 4 3 4 4 7 5 3 5 2 3 1 6 3 4                                      Wild buckwheat                                                                         8 10                                                                               10                                                                               9 8 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               6 10                                                                               3 10                                                                               9 10                                     Wild oat                                                                               4 5 3 3 1 3 3 7 3 5 5 3 4 0 5 3 2                                      __________________________________________________________________________             COMPOUND                                                               Rate 200 g/ha                                                                          26                                                                               29                                                                               30                                                                               31                                                                               33                                                                               34                                                                               35                                                                               36                                                                               41                                                                               42                                                                               43                                                                               44                                                                               45                                                                               46 47                                                                               49                                      __________________________________________________________________________     POSTEMERGENCE                                                                  Barley  4 5 4 2 3 4 6 5 3 5 3 5 2 7  3 4                                       Barnyardgrass                                                                          1 7 2 6 7 10                                                                               8 9 10                                                                               10                                                                               9 3 3 2  10                                                                               2                                       Bedstraw                                                                               4 9 4 9 10                                                                               10                                                                               9 8 9 10                                                                               10                                                                               6 7 6  10                                                                               2                                       Blackgrass                                                                             3 5 3 3 4 3 3 6 9 10                                                                               8 3 3 3  6 2                                       Cheatgrass                                                                             --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               -- --                                                                               --                                      Chickweed                                                                              1 7 3 3 6 9 6 9 10                                                                               10                                                                               9 6 4 1  9 0                                       Cocklebur                                                                              7 10                                                                               8 9 10                                                                               10                                                                               9 9 9 10                                                                               10                                                                               5 8 6  10                                                                               3                                       Corn    3 4 3 3 3 3 3 5 10                                                                               10                                                                               8 2 2 2  8 1                                       Cotton  10                                                                               10                                                                               9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10 10                                                                               5                                       Crabgrass                                                                              2 6 3 3 6 7 5 6 10                                                                               9 8 3 4 3  9 2                                       Downy brome                                                                            1 6 2 3 3 4 3 7 9 10                                                                               6 4 2 2  5 2                                       Giant foxtail                                                                          2 6 3 3 5 7 6 8 9 9 9 3 3 3  9 2                                       Lambsquarter                                                                           9 10                                                                               9 10                                                                               10                                                                               10                                                                               9 9 10                                                                               10                                                                               10                                                                               8 10                                                                               8  10                                                                               7                                       Morningglory                                                                           10                                                                               10                                                                               8 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               6  10                                                                               8                                       Nutsedge                                                                               1 5 2 5 4 4 6 8 9 9 7 2 4 6  5 0                                       Rape    5 10                                                                               3 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9 10                                                                               3  10                                                                               4                                       Rice    3 6 4 4 7 7 6 7 10                                                                               10                                                                               9 4 3 4  10                                                                               3                                       Sorghum 3 6 3 3 7 9 5 7 10                                                                               10                                                                               9 2 3 3  9 2                                       Soybean 6 9 4 8 4 9 9 9 9 10                                                                               9 8 8 7  10                                                                               5                                       Sugar beet                                                                             10                                                                               10                                                                               8 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               8 7 6  10                                                                               7                                       Velvetleaf                                                                             10                                                                               10                                                                               8 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               6 9  10                                                                               7                                       Wheat   4 5 3 3 3 5 5 4 10                                                                               9 8 3 2 2  7 3                                       Wild buckwheat                                                                         9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               4 10                                                                               5  10                                                                               3                                       Wild oat                                                                               2 5 3 2 4 7 4 6 9 10                                                                               9 4 2 2  8 2                                       __________________________________________________________________________             COMPOUND                                                               Rate 200 g/ha                                                                          3 4 5 6 8 10                                                                               11                                                                               12                                                                               14                                                                               17                                                                               18                                                                               19                                                                               20                                                                               21                                                                               22                                                                               24                                                                               25                                     __________________________________________________________________________     PREEMERGENCE                                                                   Barley  1 2 0 0 0 1 0 3 0 0 0 0 0 0 0 0 0                                      Barnyardgrass                                                                          2 8 2 2 0 7 2 8 4 0 2 0 0 0 4 0 0                                      Bedstraw                                                                               0 7 7 4 0 8 9 6 10                                                                               7 10                                                                               0 0 0 0 0 0                                      Blackgrass                                                                             1 3 0 0 1 2 2 6 1 2 2 0 0 0 3 0 0                                      Cheatgrass                                                                             --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               0 0 --                                                                               --                                                                               --                                                                               --                                     Chickweed                                                                              0 5 0 0 1 7 0 0 6 2 4 0 0 0 6 0 0                                      Cocklebur                                                                              0 0 0 0 5 2 7 2 7 0 2 3 0 0 0 0 0                                      Corn    1 2 0 0 2 4 0 3 3 0 0 0 0 0 0 0 0                                      Cotton  0 0 2 0 0 0 9 9 3 0 3 0 0 0 0 0 0                                      Crabgrass                                                                              4 8 8 3 8 8 3 8 5 0 2 0 2 0 6 1 0                                      Downy brome                                                                            1 3 3 0 2 1 2 6 2 2 2 --                                                                               --                                                                               0 4 0 0                                      Giant foxtail                                                                          2 10                                                                               3 3 5 9 3 7 5 0 2 0 0 0 7 0 0                                      Lambsquarter                                                                           9 9 10                                                                               10                                                                               10                                                                               10                                                                               9 9 10                                                                               9 9 5 0 0 10                                                                               10                                                                               9                                      Morningglory                                                                           2 8 0 0 5 4 10                                                                               6 10                                                                               0 8 6 2 0 3 0 0                                      Nutsedge                                                                               0 0 0 0 0 0 --                                                                               1 --                                                                               0 0 0 0 0 0 --                                                                               0                                      Rape    2 10                                                                               2 0 2 8 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               0 0 0 6 0 0                                      Rice    0 4 0 0 0 2 2 3 3 3 2 0 0 0 0 0 0                                      Sorghum 2 2 0 0 0 0 2 1 3 0 0 0 0 0 0 0 0                                      Soybean 0 4 0 0 0 3 3 0 4 0 0 0 0 0 1 0 0                                      Sugar beet                                                                             4 10                                                                               9 8 8 9 10                                                                               10                                                                               10                                                                               9 9 --                                                                               0 0 6 0 0                                      Velvetleaf                                                                             6 9 9 4 3 10                                                                               9 10                                                                               10                                                                               10                                                                               10                                                                               8 3 0 9 0 0                                      Wheat   0 3 0 0 0 2 0 4 2 0 0 0 0 0 3 0 0                                      Wild buckwheat                                                                         0 6 0 0 0 0 0 1 1 2 0 0 0 0 1 0 0                                      Wild oat                                                                               0 5 2 0 1 2 2 6 3 2 0 1 0 0 3 0 0                                      __________________________________________________________________________             COMPOUND                                                               Rate 200 g/ha                                                                          26                                                                               29                                                                               30                                                                               31                                                                               33                                                                               34                                                                               35                                                                               36                                                                               41                                                                               42                                                                               43                                                                               44                                                                               45                                                                               46 47                                                                               49                                      __________________________________________________________________________     PREEMERGENCE                                                                   Barley  0 3 0 2 1 0 0 1 3 6 3 0 0 0  6 0                                       Barnyardgrass                                                                          0 9 0 4 5 3 8 9 9 9 7 9 0 0  10                                                                               0                                       Bedstraw                                                                               0 5 0 0 10                                                                               9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               8 5 0  10                                                                               0                                       Blackgrass                                                                             0 3 2 2 3 2 3 3 5 10                                                                               9 0 2 0  7 0                                       Cheatgrass                                                                             --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               -- --                                                                               --                                      Chickweed                                                                              0 8 0 0 8 8 2 9 10                                                                               10                                                                               10                                                                               5 0 0  10                                                                               0                                       Cocklebur                                                                              0 7 6 2 5 6 5 8 10                                                                               10                                                                               9 0 2 0  9 1                                       Corn    0 3 0 0 3 3 1 1 9 9 9 0 2 0  7 0                                       Cotton  0 9 0 5 8 9 10                                                                               8 10                                                                               10                                                                               9 2 0 0  9 0                                       Crabgrass                                                                              0 8 0 2 3 9 9 9 10                                                                               10                                                                               10                                                                               2 5 0  9 0                                       Downy brome                                                                            0 7 3 3 6 4 6 8 9 10                                                                               9 0 0 0  10                                                                               0                                       Giant foxtail                                                                          0 10                                                                               0 7 5 10                                                                               9 10                                                                               9 10                                                                               10                                                                               8 3 0  9 0                                       Lambsquarter                                                                           7 10                                                                               3 9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9 4  10                                                                               0                                       Morningglory                                                                           0 10                                                                               0 6 10                                                                               10                                                                               10                                                                               2 10                                                                               10                                                                               10                                                                               0 3 0  10                                                                               2                                       Nutsedge                                                                               0 4 0 3 2 0 --                                                                               --                                                                               9 6 7 --                                                                               3 0  5 0                                       Rape    0 10                                                                               0 7 9 9 9 8 10                                                                               10                                                                               10                                                                               3 9 0  10                                                                               3                                       Rice    0 0 0 0 3 3 2 3 10                                                                               10                                                                               9 3 4 0  9 0                                       Sorghum 0 0 0 0 3 3 2 3 8 8 6 1 0 0  9 0                                       Soybean 0 2 0 3 10                                                                               9 4 6 8 10                                                                               7 0 2 0  8 0                                       Sugar beet                                                                             0 9 0 5 10                                                                               9 9 10                                                                               10                                                                               10                                                                               10                                                                               7 7 0  10                                                                               0                                       Velvetleaf                                                                             0 10                                                                               3 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               8 10                                                                               0  10                                                                               2                                       Wheat   0 4 0 3 1 0 1 2 6 9 9 0 0 0  6 0                                       Wild buckwheat                                                                         0 9 0 0 8 5 2 4 10                                                                               10                                                                               10                                                                               0 0 0  10                                                                               0                                       Wild oat                                                                               0 7 2 2 6 7 2 6 9 10                                                                               9 0 2 0  9 0                                       __________________________________________________________________________             COMPOUND                                                               Rate 100 g/ha                                                                          1 2 7  9 13                                                                               15                                                                               16 23                                                                               28                                                                               37                                                                               38 48                                                                               50                                                                               51                                                                               52                                      __________________________________________________________________________     POSTEMERGENCE                                                                  Barley  3 8 1  4 7 4 3  6 4 5 5  0 9 4 4                                       Barnyardgrass                                                                          9 10                                                                               2  3 9 4 8  9 5 10                                                                               8  5 8 6 7                                       Bedstraw                                                                               8 9 3  8 8 8 9  9 10                                                                               10                                                                               9  6 8 4 6                                       Blackgrass                                                                             4 9 1  2 6 3 3  5 4 6 5  0 7 5 4                                       Cheatgrass                                                                             --                                                                               --                                                                               -- --                                                                               --                                                                               --                                                                               -- --                                                                               --                                                                               --                                                                               -- --                                                                               --                                                                               --                                                                               --                                      Chickweed                                                                              4 10                                                                               1  2 6 4 3  9 2 8 5  2 9 3 3                                       Cocklebur                                                                              7 10                                                                               1  7 8 9 7  10                                                                               9 9 10 6 9 3 10                                      Corn    4 8 2  2 3 2 6  3 2 5 3  2 1 1 3                                       Cotton  10                                                                               10                                                                               9  9 10                                                                               10                                                                               10 10                                                                               10                                                                               10                                                                               10 9 9 7 9                                       Crabgrass                                                                              5 9 2  6 7 5 4  8 2 6 7  2 4 3 3                                       Downy brome                                                                            3 7 0  2 7 3 2  4 2 6 4  0 8 3 5                                       Giant foxtail                                                                          5 9 1  4 8 3 7  9 3 8 7  2 5 2 6                                       Lambsquarter                                                                           10                                                                               10                                                                               3  9 8 9 6  10                                                                               8 10                                                                               9  4 9 9 9                                       Morningglory                                                                           9 10                                                                               8  9 9 9 10 10                                                                               10                                                                               10                                                                               10 9 10                                                                               10                                                                               10                                      Nutsedge                                                                               1 4 1  4 8 --                                                                               5  1 2 2 2  0 2 --                                                                               2                                       Rape    6 10                                                                               2  9 9 10                                                                               10 10                                                                               9 10                                                                               10 2 10                                                                               10                                                                               10                                      Rice    6 10                                                                               1  6 9 6 5  8 4 4 6  0 8 3 7                                       Sorghum 4 9 2  3 6 4 5  9 5 4 4  2 4 3 3                                       Soybean 9 9 3  7 8 8 3  9 8 8 8  4 2 6 8                                       Sugar beet                                                                             9 10                                                                               3  9 10                                                                               9 8  9 10                                                                               10                                                                               10 8 10                                                                               10                                                                               9                                       Velvetleaf                                                                             9 10                                                                               8  9 10                                                                               10                                                                               10 10                                                                               10                                                                               10                                                                               10 1 9 8 10                                      Wheat   4 9 1  3 7 5 3  5 4 5 4  2 9 5 9                                       Wild buckwheat                                                                         10                                                                               10                                                                               3  9 8 10                                                                               6  10                                                                               9 10                                                                               9  3 10                                                                               10                                                                               10                                      Wild oat                                                                               4 8 0  2 8 4 2  7 2 5 4  0 6 3 4                                       PREEMERGENCE                                                                   Barley  1 4 0  3 7 0 0  3 0 0 0  0 3 0 3                                       Barnyardgrass                                                                          7 9 0  7 10                                                                               0 0  9 0 2 0  0 0 0 2                                       Bedstraw                                                                               1 10                                                                               2  2 7 8 0  10                                                                               0 7 0  0 3 0 3                                       Blackgrass                                                                             2 7 0  0 6 2 0  4 0 5 5  1 0 0 3                                       Cheatgrass                                                                             --                                                                               --                                                                               -- --                                                                               --                                                                               --                                                                               -- --                                                                               --                                                                               --                                                                               -- --                                                                               --                                                                               --                                                                               --                                      Chickweed                                                                              1 10                                                                               0  0 6 3 0  8 0 0 0  0 2 0 0                                       Cocklebur                                                                              2 10                                                                               0  3 9 0 0  --                                                                               0 2 0  3 0 0 6                                       Corn    1 6 0  3 7 0 0  1 0 1 0  0 0 0 0                                       Cotton  2 9 0  0 4 0 0  8 0 1 0  0 0 0 0                                       Crabgrass                                                                              9 10                                                                               0  6 8 0 0  9 1 7 1  0 0 0 9                                       Downy brome                                                                            1 7 0  2 6 3 0  9 2 3 3  1 3 2 2                                       Giant foxtail                                                                          9 10                                                                               0  10                                                                               9 0 0  9 3 9 4  0 0 0 0                                       Lambsquarter                                                                           10                                                                               10                                                                               0  8 9 9 0  10                                                                               10                                                                               10                                                                               9  7 9 6 6                                       Morningglory                                                                           0 10                                                                               0  3 10                                                                               0 4  10                                                                               0 6 2  0 10                                                                               0 10                                      Nutsedge                                                                               0 --                                                                               0  0 2 0 -- 0 0 0 0  3 0 0 0                                       Rape    8 10                                                                               0  10                                                                               10                                                                               6 1  10                                                                               2 8 3  0 7 3 0                                       Rice    1 3 0  4 8 0 0  3 0 2 0  0 0 0 2                                       Sorghum 3 4 0  0 7 0 0  2 0 0 0  0 0 0 0                                       Soybean 4 9 0  3 6 0 0  0 0 1 0  0 0 0 0                                       Sugar beet                                                                             6 10                                                                               3  7 10                                                                               9 2  8 3 10                                                                               6  3 8 7 5                                       Velvetleaf                                                                             10                                                                               10                                                                               0  10                                                                               10                                                                               0 0  10                                                                               0 10                                                                               10 0 0 0 0                                       Wheat   0 5 0  3 8 2 0  6 0 0 3  0 3 0 3                                       Wild buckwheat                                                                         4 10                                                                               0  1 3 4 0  8 4 2 0  0 2 0 0                                       Wild oat                                                                               4 8 0  3 7 3 0  6 0 7 3  0 3 2 5                                       __________________________________________________________________________             COMPOUND                                                               Rate 50 g/ha                                                                           3 4 5 6 8 10                                                                               11                                                                               12                                                                               14                                                                               17                                                                               18                                                                               19                                                                               20                                                                               21 22                                                                               24                                      __________________________________________________________________________     POSTEMERGENCE                                                                  Barley  3 5 3 3 2 3 3 5 5 3 5 2 3 1  5 3                                       Barnyardgrass                                                                          2 6 3 2 3 3 7 2 2 3 7 2 3 2  5 2                                       Bedstraw                                                                               3 9 7 6 4 7 10                                                                               7 7 9 10                                                                               4 7 4  9 5                                       Blackgrass                                                                             2 4 3 2 2 2 2 4 3 3 3 1 2 3  2 3                                       Cheatgrass                                                                             --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               0 1 -- --                                                                               --                                      Chickweed                                                                              2 7 3 1 2 4 1 6 5 3 3 3 2 1  6 2                                       Cocklebur                                                                              1 7 4 4 7 7 8 7 8 6 8 6 8 1  9 7                                       Corn    2 6 3 3 2 2 5 3 2 6 9 4 2 1  1 2                                       Cotton  3 10                                                                               9 9 9 10                                                                               10                                                                               9 9 10                                                                               10                                                                               10                                                                               10                                                                               10 10                                                                               10                                      Crabgrass                                                                              3 4 2 2 3 4 3 3 3 2 6 5 4 1  1 2                                       Downy brome                                                                            1 4 3 3 2 3 3 3 2 3 3 --                                                                               --                                                                               2  3 2                                       Giant foxtail                                                                          2 4 3 3 3 4 5 2 3 3 5 3 4 1  2 2                                       Lambsquarter                                                                           6 8 9 5 9 8 9 8 8 9 8 4 6 3  9 4                                       Morningglory                                                                           3 9 7 6 7 8 9 9 8 9 10                                                                               5 9 5  10                                                                               6                                       Nutsedge                                                                               0 4 1 1 0 1 4 1 3 --                                                                               --                                                                               --                                                                               --                                                                               -- 0 1                                       Rape    5 10                                                                               5 5 3 6 9 6 9 8 10                                                                               3 7 5  8 3                                       Rice    3 7 5 5 3 6 5 5 6 6 6 6 4 4  5 3                                       Sorghum 3 3 3 3 2 3 5 2 2 6 6 3 3 2  3 2                                       Soybean 5 8 4 5 3 8 3 8 7 4 8 6 7 3  6 --                                      Sugar beet                                                                             6 10                                                                               10                                                                               8 9 10                                                                               10                                                                               9 10                                                                               10                                                                               10                                                                               4 6 2  8 8                                       Velvetleaf                                                                             3 10                                                                               9 8 4 9 10                                                                               6 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               1  10                                                                               8                                       Wheat   2 5 3 2 2 3 2 36                                                                               4 4 4 1 2 1  3 3                                       Wild buckwheat                                                                         4 10                                                                               7 5 7 9 9 8 7 9 10                                                                               6 9 1  9 6                                       Wild oat                                                                               3 4 4 2 1 2 2 3 4 4 4 2 1 0  2 3                                       __________________________________________________________________________             COMPOUND                                                               Rate 50 g/ha                                                                           25                                                                               26                                                                               29                                                                               30                                                                               31                                                                               33                                                                               34                                                                               35                                                                               36                                                                               42                                                                               43                                                                               44                                                                               45                                                                               46 47                                                                               49                                      __________________________________________________________________________     POSTEMERGENCE                                                                  Barley  3 2 5 2 3 5 5 3 4 7 5 2 1 2  4 0                                       Barnyardgrass                                                                          2 1 5 2 1 4 8 4 7 9 9 1 2 2  9 1                                       Bedstraw                                                                               4 4 8 2 5 10                                                                               9 8 9 10                                                                               9 4 6 3  10                                                                               2                                       Blackgrass                                                                             3 2 4 2 3 3 3 3 2 9 6 1 2 0  2 1                                       Cheatgrass                                                                             --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               -- --                                                                               --                                      Chickweed                                                                              1 1 8 1 2 6 7 3 9 10                                                                               8 5 5 1  8 0                                       Cocklebur                                                                              7 6 10                                                                               6 8 10                                                                               9 8 8 9 9 3 7 6  9 3                                       Corn    2 2 2 2 2 3 3 3 2 9 7 2 2 1  5 0                                       Cotton  10                                                                               10                                                                               10                                                                               7 9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               5 10 10                                                                               5                                       Crabgrass                                                                              2 2 4 3 3 6 6 3 5 9 7 2 3 2  7 1                                       Downy brome                                                                            2 1 3 2 2 2 3 3 3 8 4 1 1 0  3 0                                       Giant foxtail                                                                          3 2 4 3 3 4 5 3 6 9 8 2 2 2  8 1                                       Lambsquarter                                                                           8 7 10                                                                               8 9 10                                                                               10                                                                               7 9 10                                                                               8 8 8 4  10                                                                               4                                       Morningglory                                                                           7 7 10                                                                               6 10                                                                               9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9 8 2  10                                                                               3                                       Nutsedge                                                                               1 1 3 2 3 --                                                                               --                                                                               2 2 6 5 --                                                                               2 0  2 0                                       Rape    6 5 10                                                                               1 8 10                                                                               10                                                                               9 9 10                                                                               9 6 8 2  10                                                                               2                                       Rice    3 3 5 3 4 5 6 5 6 10                                                                               9 3 3 2  8 2                                       Sorghum 3 3 4 2 3 46                                                                               6 4 5 9 9 2 2 2  7 2                                       Soybean 3 3 8 3 5 4 9 8 9 9 5 8 8 5  9 3                                       Sugar beet                                                                             10                                                                               8 10                                                                               3 10                                                                               10                                                                               9 9 10                                                                               10                                                                               10                                                                               8 7 2  10                                                                               4                                       Velvetleaf                                                                             10                                                                               10                                                                               10                                                                               5 5 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               4 2 3  10                                                                               1                                       Wheat   3 2 5 2 3 3 4 4 3 7 6 1 0 1  5 1                                       Wild buckwheat                                                                         9 8 10                                                                               6 9 10                                                                               10                                                                               9 10                                                                               10                                                                               10                                                                               3 9 3  10                                                                               2                                       Wild oat                                                                               1 1 5 2 2 4 5 4 4 9 6 2 2 1  5 0                                       __________________________________________________________________________             COMPOUND                                                               Rate 50 g/ha                                                                           3 4 5 6 8 10                                                                               11                                                                               12                                                                               14                                                                               17                                                                               18                                                                               19                                                                               20                                                                               21 22                                                                               24                                      __________________________________________________________________________     PREEMERGENCE                                                                   Barley  0 0 0 0 0 0 0 0 0 0 0 0 0 0  0 0                                       Barnyardgrass                                                                          2 5 0 0 0 0 0 0 0 0 0 0 0 0  2 0                                       Bedstraw                                                                               0 3 4 4 --                                                                               3 2 5 4 0 9 0 0 0  0 0                                       Blackgrass                                                                             1 0 0 0 0 1 0 0 1 0 0 0 0 0  0 0                                       Cheatgrass                                                                             --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               0 0 -- --                                                                               --                                      Chickweed                                                                              0 2 0 0 0 2 0 0 3 2 4 0 0 0  3 0                                       Cocklebur                                                                              0 0 0 0 3 0 0 0 3 0 0 0 0 0  0 0                                       Corn    0 0 0 0 0 2 0 2 0 0 0 0 0 0  0 0                                       Cotton  0 0 0 0 0 0 3 4 0 0 0 0 0 0  0 0                                       Crabgrass                                                                              2 0 3 3 2 6 0 1 2 0 2 0 0 0  3 0                                       Downy brome                                                                            0 2 0 0 0 1 0 0 0 0 2 --                                                                               --                                                                               0  0 0                                       Giant foxtail                                                                          0 3 0 0 0 6 0 0 2 0 0 0 0 0  2 0                                       Lambsquarter                                                                           2 6 9 9 8 10                                                                               8 7 10                                                                               8 6 3 0 0  10                                                                               0                                       Morningglory                                                                           0 9 0 0 0 4 10                                                                               3 4 0 4 3 0 0  0 0                                       Nutsedge                                                                               0 0 0 0 0 0 0 0 --                                                                               0 0 0 0 0  0 0                                       Rape    0 10                                                                               0 0 0 0 9 3 10                                                                               9 6 0 0 0  2 0                                       Rice    0 2 0 0 0 0 0 0 0 0 0 0 0 0  0 0                                       Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0  0 0                                       Soybean 0 0 0 0 0 3 0 0 0 0 0 0 0 0  0 0                                       Sugar beet                                                                             0 9 6 4 7 8 10                                                                               4 9 9 9 0 0 0  6 0                                       Velvetleaf                                                                             3 2 0 0 0 9 2 9 10                                                                               0 3 4 0 0  2 0                                       Wheat   0 2 0 0 0 0 0 0 1 0 0 0 0 0  0 0                                       Wild buckwheat                                                                         0 3 0 0 0 0 0 0 0 0 0 0 0 0  0 0                                       Wild oat                                                                               0 0 0 0 0 1 0 0 0 0 2 0 0 0  0 0                                       __________________________________________________________________________             COMPOUND                                                               Rate 50 g/ha                                                                           25                                                                               26                                                                               29                                                                               30                                                                               31                                                                               33                                                                               34                                                                               35                                                                               36                                                                               42                                                                               43                                                                               44                                                                               45                                                                               46 47                                                                               494                                     __________________________________________________________________________     PREEMERGENCE                                                                   Barley  0 0 1 0 0 0 0 --                                                                               0 5 3 0 0 0  2 0                                       Barnyardgrass                                                                          0 0 3 0 0 0 0 2 2 9 8 0 0 0  9 0                                       Bedstraw                                                                               0 0 5 0 0 6 9 9 9 10                                                                               10                                                                               0 0 0  10                                                                               0                                       Blackgrass                                                                             0 0 3 0 0 0 2 0 1 9 7 0 2 0  3 0                                       Cheatgrass                                                                             --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               --                                                                               -- --                                                                               --                                      Chickweed                                                                              0 0 6 0 0 2 3 0 0 10                                                                               9 0 0 0  9 0                                       Cocklebur                                                                              0 0 3 0 --                                                                               3 3 0 3 10                                                                               5 0 0 0  6 0                                       Corn    0 0 2 0 0 2 2 0 0 9 5 0 0 0  8 0                                       Cotton  0 0 4 0 0 4 0 0 0 10                                                                               6 0 0 0  8 0                                       Crabgrass                                                                              0 0 2 0 0 3 8 5 8 10                                                                               8 0 0 0  8 0                                       Downy brome                                                                            0 0 3 0 2 3 5 2 2 8 5 0 1 0  2 0                                       Giant foxtail                                                                          0 0 8 0 0 3 8 7 9 9 8 0 0 0  7 0                                       Lambsquarter                                                                           0 0 10                                                                               0 9 9 10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               10                                                                               9 0  10                                                                               0                                       Morningglory                                                                           0 0 5 0 0 0 6 0 0 10                                                                               10                                                                               0 2 0  10                                                                               0                                       Nutsedge                                                                               0 0 0 0 0 0 0 0 --                                                                               6 --                                                                               --                                                                               5 0  3 0                                       Rape    0 0 7 0 0 2 9 5 6 10                                                                               10                                                                               0 2 0  10                                                                               0                                       Rice    0 0 0 0 0 2 2 0 2 9 7 0 0 0  8 0                                       Sorghum 0 0 0 0 0 2 0 0 0 6 5 0 0 0  8 0                                       Soybean 0 0 0 0 0 5 3 2 0 7 6 0 0 0  6 0                                       Sugar beet                                                                             0 0 6 0 0 6 7 8 9 10                                                                               10                                                                               0 7 0  10                                                                               0                                       Velvetleaf                                                                             0 0 3 0 0 0 0 1 1 6 6 0 0 0  3 0                                       Wheat   0 0 3 0 0 0 0 1 1 6 6 0 0 0  3 0                                       Wild buckwheat                                                                         0 0 6 0 0 0 0 0 0 10                                                                               5 0 0 0  2 0                                       Wild oat                                                                               0 0 4 0 0 5 6 1 3 9 9 0 0 0  6 0                                       __________________________________________________________________________             COMPOUND                                                               Rate 20 g/ha                                                                           7  13 15 16 28 37 38 48 50 51 52                                       __________________________________________________________________________     POSTEMERGENCE                                                                  Barley  0  4  3  2  3  4  4  0  5  3  5                                        Barnyardgrass                                                                          1  8  3  5  5  6  7  1  6  4  5                                        Bedstraw                                                                               3  8  6  5  4  9  8  2  7  2  3                                        Blackgrass                                                                             1  3  2  2  3  4  4  0  5  2  3                                        Cheatgrass                                                                             -- -- -- -- -- -- -- -- -- -- --                                       Chickweed                                                                              0  4  3  2  2  6  5  0  7  2  3                                        Cocklebur                                                                              0  7  8  6  6  7  10 2  4  2  4                                        Corn    1  2  2  2  2  4  2  1  1  1  2                                        Cotton  7  10 10 10 9  10 10 9  7  3  9                                        Crabgrass                                                                              0  4  3  3  2  6  6  2  2  1  3                                        Downy brome                                                                            0  2  3  2  2  5  4  0  7  2  4                                        Giant foxtail                                                                          0  4  3  3  3  6  5  3  2  1  2                                        Lambsquarter                                                                           4  6  8  4  6  8  8  2  8  8  8                                        Morningglory                                                                           2  9  10 6  9  10 10 7  9  10 10                                       Nutsedge                                                                               0  4  -- 4  -- 0  0  0  0  0  1                                        Rape    1  6  8  8  5  9  8  2  8  6  10                                       Rice    1  8  5  3  3  3  3  3  3  2  3                                        Sorghum 2  3  3  3  3  4  3  3  3  2  3                                        Soybean 1  7  7  3  4  8  8  3  2  5  4                                        Sugar beet                                                                             2  10 10 5  6  8  9  3  8  9  8                                        Velvetleaf                                                                             1  10 10 5  8  10 10 1  4  2  4                                        Wheat   0  5  3  2  4  4  3  0  7  3  6                                        Wild buckwheat                                                                         2  7  8  6  8  9  10 3  10 7  4                                        Wild oat                                                                               0  3  3  1  1  3  3  0  4  3  3                                        PREEMERGENCE                                                                   Barley  0  1  3  0  0  2  0  0  0  0  0                                        Barnyardgrass                                                                          0  8  0  0  0  0  0  0  0  0  0                                        Bedstraw                                                                               0  3  8  -- 0  0  0  0  0  0  0                                        Blackgrass                                                                             0  3  2  0  0  2  2  0  0  0  0                                        Cheatgrass                                                                             -- -- -- -- -- -- -- -- -- -- --                                       Chickweed                                                                              0  2  -- 0  0  0  0  0  0  0  0                                        Cocklebur                                                                              0  5  0  0  0  0  0  0  0  0  0                                        Corn    0  4  0  0  0  0  0  0  0  0  0                                        Cotton  0  4  0  0  0  0  0  0  0  0  0                                        Crabgrass                                                                              0  3  0  0  0  2  0  0  0  0  0                                        Downy brome                                                                            0  4  -- 0  0  2  2  0  2  0  0                                        Giant foxtail                                                                          0  7  0  0  0  3  0  0  0  0  0                                        Lambsquarter                                                                           0  9  -- 0  0  7  9  -- 2  0  0                                        Morningglory                                                                           0  3  0  0  0  0  0  0  6  0  0                                        Nutsedge                                                                               0  0  0  -- 0  0  0  -- 0  0  0                                        Rape    0  8  2  0  0  2  0  0  3  0  0                                        Rice    0  7  0  0  0  0  0  0  0  0  0                                        Sorghum 0  1  0  0  0  0  0  0  0  0  0                                        Soybean 0  5  0  0  0  0  0  0  0  0  0                                        Sugar beet                                                                             0  9  3  0  0  2  0  0  3  0  0                                        Velvetleaf                                                                             0  9  0  0  0  8  4  0  0  0  0                                        Wheat   0  3  2  0  0  2  0  0  0  0  1                                        Wild buckwheat                                                                         0  0  3  0  0  0  0  0  0  0  0                                        Wild oat                                                                               0  3  2  0  0  3  0  0  0  0  1                                        __________________________________________________________________________

TEST B

Seeds of barnyardgrass (Echinochloa crus-galli), cocklebur (Xanthium pensylvanicum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), morningglory (Ipomoea spp.), sorghum (Sorghum bicolor), velvetleaf (Abutilon theophrasti), and wild oat (Avena fatua) were planted into a sandy loam soil and treated preemergence or by soil drench, with test chemicals formulated in a non-phytotoxic solvent mixture which includes a surfactant. At the same time, these crop and weed species were also treated postemergence or sprayed to runoff, with test chemicals formulated in the same manner. Plants ranged in height from two to eighteen cm and were in the two to three leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately eleven days, after which all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table B, are based on a 0 to 10 scale where 0 is no effect and 10 is complete control. A dash (-) response means no test results.

    ______________________________________                                                           COMPOUND                                                     Rate 2000 g/ha    27     49                                                    ______________________________________                                         SOIL DRENCH                                                                    Barnyardgrass     9      8                                                     Cocklebur         7      5                                                     Crabgrass         9      3                                                     Downy brome       7      2                                                     Giant foxtail     10     5                                                     Morningglory      10     10                                                    Sorghum           5      2                                                     Velvetleaf        10     7                                                     Wild oats         5      0                                                     ______________________________________                                                           COMPOUND                                                     Rate 1000 g/ha    27     49                                                    ______________________________________                                         SPRAYED TO RUNOFF                                                              Barnyardgrass     7      4                                                     Cocklebur         10     10                                                    Crabgrass         5      4                                                     Downy brome       8      7                                                     Giant foxtail     7      6                                                     Morningglory      10     10                                                    Sorghum           6      3                                                     Velvetleaf        10     10                                                    Wild oats         3      4                                                     ______________________________________                                    

TEST C

The compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which includes a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (flood application), and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the flood test. Water depth was approximately 2.5 cm for the flood test and was maintained at this level for the duration of the test.

Plant species in the preemergence and postemergence tests consisted of barnyardgrass (Echinochloa crus-galli), barley (Hordeum vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setaria faberii), johnsongrass (Sorghum halpense), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), pigweed (Amaranthus retroflexus), rape (Brassica napus), ryegrass (Lolium multiflorum), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua). All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test. Plant species in the flood test consisted of rice (Oryza sativa), umbrella sedge (Cyperus difformis), duck salad (Heteranthera limosa), barnyard 2 (Echinochloa crus-galli) and watergrass 2 (Echinocloa oryzicola) grown to the 1 and 2 leaf stage for testing.

All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to untreated controls, were recorded approximately fourteen to twenty one days after application of the test compound. Plant response ratings summarized in Table C, were recorded on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

                                      TABLE C                                      __________________________________________________________________________     Rate 250 g/ha   COMPOUND 4  Rate 250 g/ha  COMPOUND 4                          __________________________________________________________________________     POSTEMERGENCE               PREEMERGENCE                                       Barley Igri     35          Barley Igri    10                                  Barnyard 2      85          Barnyardgrass  90                                  Barnyardgrass   95          Bedstraw       75                                  Bedstraw        85          Blackgrass     40                                  Blackgrass      55          Chickweed      80                                  Chickweed       95          Cocklebur      40                                  Cocklebur       100         Corn           20                                  Corn            35          Cotton         30                                  Cotton          100         Crabgrass      70                                  Crabgrass       40          Downy Brome    0                                   Downy Brome     35          Giant foxtail  100                                 Duck salad      0           Italn. Rygrass 0                                   Giant foxtail   85          Johnsongrass   20                                  Italn. Rygrass  65          Lambsquarter   90                                  Johnsongrass    90          Morningglory   70                                  Lambsquarter    70          Rape           100                                 Morningglory    100         Redroot Pigweed                                                                               100                                 Rape            100         Soybean        50                                  Redroot Pigweed 100         Speedwell      100                                 Rice            95          Sugar beet     100                                 Soybean         100         Velvetleaf     100                                 Speedwell       --          Wheat          0                                   Sugar beet      --          Wild buckwheat 100                                 Umbrella sedge  15          Wild oat       30                                  Velvetleaf      100                                                            Watergrass 2    85                                                             Wheat           30                                                             Wild buckwheat  100                                                            Wild oat        40                                                             __________________________________________________________________________                    COMPOUND                                                        Rate 125 g/ha  1       4       9       23      41                              __________________________________________________________________________     POSTEMERGENCE                                                                  Barley Igri    --      35      30      55      95                              Barnyard 2     20      40      10      100     70                              Barnyardgrass  --      40      80      95      95                              Bedstraw       --      70      0       100     100                             Blackgrass     --      50      0       80      65                              Chickweed      --      95      10      100     100                             Cocklebur      --      85      35      100     100                             Corn           --      30      25      35      90                              Cotton         --      100     95      100     100                             Crabgrass      --      35      25      85      95                              Downy Brome    --      35      20      85      100                             Duck salad     0       0       0       50      0                               Giant foxtail  --      65      65      100     100                             Italn. Rygrass --      30      20      95      100                             Johnsongrass   --      80      30      90      100                             Lambsquarter   --      70      90      100     100                             Morningglory   --      100     90      100     100                             Rape           --      100     100     100     100                             Redroot Pigweed                                                                               --      100     75      100     100                             Rice           45      70      20      100     95                              Soybean        --      75      50      100     80                              Speedwell      --      --      100     100     --                              Sugar beet     --      100     40      100     100                             Umbrella sedge 0       0       0       50      0                               Velvetleaf     --      100     100     100     100                             Watergrass 2   15      80      0       100     95                              Wheat          --      30      20      50      100                             Wild buckwheat --      100     85      100     100                             Wild oat       --      30      20      75      95                              PREEMERGENCE                                                                   Barley Igri    0       10      50      70      80                              Barnyardgrass  90      25      35      100     95                              Bedstraw       100     15      10      100     100                             Blackgrass     55      30      0       80      95                              Chickweed      20      60      20      100     100                             Cocklebur      0       30      25      85      100                             Corn           10      0       20      50      55                              Cotton         10      25      35      100     100                             Crabgrass      90      50      70      100     100                             Downy Brome    0       0       10      80      60                              Giant foxtail  95      100     95      100     100                             Italn. Rygrass 60      0       20      90      100                             Johnsongrass   90      15      20      95      100                             Lambsquarter   100     85      70      100     100                             Morningglory   20      --      60      100     100                             Rape           10      100     100     100     100                             Redroot Pigweed                                                                               100     100     80      100     100                             Soybean        30      30      10      40      95                              Speedwell      100     100     90      100     100                             Sugar beet     100     100     45      100     100                             Velvetleaf     100     100     100     100     100                             Wheat          0       0       10      65      100                             Wild buckwheat 10      90      30      100     100                             Wild oat       20      10      50      65      90                              __________________________________________________________________________                COMPOUND                                                            Rate 62 g/ha                                                                              1  2  4  9  18 22 23 29 33 34 35 36 41  43                          __________________________________________________________________________     POSTEMERGENCE                                                                  Barley Igri                                                                               -- 55 30 20 35 35 55 75 45 65 55 50 95  65                          Barnyard 2 10 95 20 0  20 85 100                                                                               85 85 95 40 70 60  10                          Barnyardgrass                                                                             -- 80 10 40 35 30 95 80 60 80 70 90 65  85                          Bedstraw   -- 100                                                                               65 0  25 20 100                                                                               100                                                                               95 100                                                                               95 95 100 85                          Blackgrass -- 80 40 0  10 45 70 40 50 75 40 65 35  65                          Chickweed  -- 100                                                                               75 10 50 50 95 90 100                                                                               95 90 100                                                                               100 100                         Cocklebur  -- 100                                                                               80 25 70 60 100                                                                               100                                                                               100                                                                               100                                                                               90 90 85  --                          Corn       -- 65 30 25 55 30 30 35 40 25 30 30 65  80                          Cotton     -- 100                                                                               100                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100 100                         Crabgrass  -- 100                                                                               30 10 35 20 85 50 30 50 50 80 65  60                          Downy Brome                                                                               -- 65 30 0  45 0  75 45 65 80 60 85 100 40                          Duck salad 0  0  0  0  0  25 0  0  30 35 0  0  0   0                           Giant foxtail                                                                             -- 100                                                                               30 30 65 60 95 60 50 60 75 65 85  70                          Italn. Rygrass                                                                            -- 90 30 0  0  0  90 65 75 70 50 75 95  90                          Johnsongrass                                                                              -- 100                                                                               60 20 90 50 90 60 50 80 50 70 95  95                          Lambsquarter                                                                              -- 100                                                                               65 90 100                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               70  100                         Morningglory                                                                              -- 100                                                                               100                                                                               70 100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               95 100                                                                               100 100                         Rape       -- 100                                                                               100                                                                               95 100                                                                               35 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100 100                         Redroot Pigweed                                                                           -- 100                                                                               100                                                                               70 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100 100                         Rice       40 95 60 20 25 25 95 50 70 75 35 55 90  10                          Soybean    -- 100                                                                               75 50 65 90 100                                                                               90 60 100                                                                               90 90 80  100                         Speedwell  -- 100                                                                               -- 95 100                                                                               40 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               --  100                         Sugar beet -- 100                                                                               100                                                                               40 100                                                                               95 100                                                                               -- 100                                                                               100                                                                               100                                                                               100                                                                               100 100                         Umbrella sedge                                                                            0  50 -- 0  0  0  0  0  25 30 0  0  0   0                           Velvetleaf -- 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100 100                         Watergrass 2                                                                              10 90 25 0  30 30 100                                                                               45 85 65 30 65 85  10                          Wheat      -- 60 30 15 35 35 50 65 65 65 65 70 95  80                          Wild buckwheat                                                                            -- 100                                                                               95 80 85 95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100 100                         Wild oat   -- 70 30 10 30 0  70 80 50 70 60 65 95  80                          PREEMERGENCE                                                                   Barley Igri                                                                               0  10 0  30 0  0  30 0  0  25 0  35 80  70                          Barnyardgrass                                                                             65 80 25 20 0  10 100                                                                               10 0  20 0  80 90  95                          Bedstraw   0  100                                                                               10 10 0  0  100                                                                               0  25 100                                                                               90 0  100 100                         Blackgrass 10 80 25 0  10 0  70 35 0  0  0  30 85  70                          Chickweed  20 95 30 -- 0  0  100                                                                               85 0  95 10 90 100 100                         Cocklebur  0  70 20 10 0  0  60 20 20 35 0  0  60  100                         Corn       0  65 0  0  0  10 50 10 10 0  0  0  55  60                          Cotton     0  100                                                                               20 0  0  25 60 0  30 70 0  0  90  90                          Crabgrass  30 100                                                                               20 70 0  55 100                                                                               75 10 20 10 50 95  85                          Downy Brome                                                                               0  55 0  10 10 10 10 0  0  0  0  25 60  60                          Giant foxtail                                                                             50 100                                                                               80 55 0  10 95 60 0  100                                                                               30 90 95  100                         Italn. Rygrass                                                                            10 85 0  15 0  0  80 0  10 30 30 70 95  90                          Johnsongrass                                                                              20 90 0  10 0  20 85 0  0  20 0  20 95  95                          Lambsquarter                                                                              100                                                                               100                                                                               50 50 20 0  100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100 100                         Morningglory                                                                              10 100                                                                               60 -- 0  50 75 10 80 60 20 70 100 80                          Rape       0  100                                                                               60 90 0  0  60 0  10 25 10 10 100 100                         Redroot Pigweed                                                                           100                                                                               100                                                                               100                                                                               35 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100 100                         Soybean    30 100                                                                               0  0  0  40 35 0  25 20 0  0  15  0                           Speedwell  100                                                                               100                                                                               30 85 85 20 100                                                                               95 95 95 100                                                                               95 100 100                         Sugar beet 20 100                                                                               100                                                                               35 25 10 100                                                                               10 35 100                                                                               10 100                                                                               100 100                         Velvetleaf 100                                                                               100                                                                               50 85 20 60 100                                                                               100                                                                               100                                                                               100                                                                               80 100                                                                               100 100                         Wheat      -- 55 0  0  0  0  20 20 0  0  0  40 80  90                          Wild buckwheat                                                                            0  100                                                                               70 10 0  0  100                                                                               35 30 100                                                                               25 50 75  90                          Wild oat   20 65 0  30 15 0  60 0  0  25 50 65 80  80                          __________________________________________________________________________               COMPOUND                                                             Rate 31 g/ha                                                                             1  2  4  9  18 22 23 29 33 34 35 36 41 42 43                         __________________________________________________________________________     POSTEMERGENCE                                                                  Barley Igri                                                                              -- 50 30 20 30 30 55 60 45 60 55 50 75 65 50                         Barnyard 2                                                                               10 90 0  0  15 25 85 65 70 75 30 35 25 100                                                                               0                          Barnyardgrass                                                                            -- 75 10 0  30 20 90 60 60 70 50 30 0  95 85                         Bedstraw  -- 100                                                                               65 0  25 10 100                                                                               95 90 100                                                                               90 90 100                                                                               100                                                                               75                         Blackgrass                                                                               -- 70 35 0  10 0  60 40 50 75 40 65 35 75 65                         Chickweed -- 95 75 0  50 50 95 75 95 95 80 95 100                                                                               95 70                         Cocklebur -- 100                                                                               60 10 60 60 100                                                                               90 90 90 70 90 -- 100                                                                               90                         Corn      -- 65 30 10 35 20 25 30 30 25 30 25 35 85 65                         Cotton    -- 100                                                                               100                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                        Crabgrass -- 85 25 0  30 15 80 20 -- 50 30 30 65 80 60                         Downy Brome                                                                              -- 60 30 0  0  0  60 30 55 75 60 70 35 65 25                         Duck salad                                                                               0  0  0  0  0  10 0  0  0  20 0  0  0  0  0                          Giant foxtail                                                                            -- 95 30 0  50 30 90 50 50 50 35 35 75 90 70                         Italn. Rygrass                                                                           -- 85 10 0  0  0  80 65 70 65 50 70 70 95 90                         Johnsongrass                                                                             -- 95 40 10 75 30 80 40 50 60 30 60 40 90 90                         Lambsquarter                                                                             -- 100                                                                               65 70 65 50 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               65 100                                                                               95                         Morningglory                                                                             -- 100                                                                               100                                                                               45 100                                                                               80 100                                                                               100                                                                               95 100                                                                               -- 90 100                                                                               100                                                                               100                        Rape      -- 100                                                                               100                                                                               75 90 0  100                                                                               95 100                                                                               100                                                                               95 100                                                                               100                                                                               100                                                                               85                         Redroot Pigweed                                                                          -- 100                                                                               100                                                                               50 -- 90 100                                                                               100                                                                               100                                                                               100                                                                               95 100                                                                               100                                                                               100                                                                               100                        Rice      35 90 30 10 0  30 75 45 60 65 25 35 60 80 10                         Soybean   -- 95 75 25 55 -- 90 60 50 100                                                                               80 80 80 90 70                         Speedwell -- 100                                                                               -- 95 100                                                                               -- 100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               -- 100                                                                               100                        Sugar beet                                                                               -- 100                                                                               80 30 60 90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               95 100                                                                               100                        Umbrella sedge                                                                           0  50 0  0  0  0  0  0  20 0  0  0  0  0  0                          Velvetleaf                                                                               -- 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                        Watergrass 2                                                                             10 55 20 0  30 25 75 25 75 55 25 55 25 10 0                          Wheat     -- 50 30 15 35 35 40 50 50 45 45 55 65 85 70                         Wild buckwheat                                                                           -- 100                                                                               80 65 40 40 100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               100                                                                               100                                                                               100                        Wild oat  -- 50 30 10 30 0  65 65 50 70 60 60 35 90 70                         PREEMERGENCE                                                                   Barley Igri                                                                              0  0  0  10 0  0  30 0  0  0  0  10 70 75 50                         Barnyardgrass                                                                            -- 70 10 15 0  0  90 10 0  10 0  20 90 95 90                         Bedstraw  0  100                                                                               0  10 0  0  90 -- 25 95 10 0  100                                                                               100                                                                               100                        Blackgrass                                                                               10 80 30 0  0  0  55 10 0  0  0  10 60 90 60                         Chickweed 10 55 0  0  0  0  0  0  0  85 10 25 100                                                                               100                                                                               80                         Cocklebur 0  -- 0  0  0  0  50 0  0  20 0  0  45 100                                                                               20                         Corn      0  35 0  0  0  0  20 0  0  0  0  0  55 60 50                         Cotton    -- 70 0  0  0  10 50 0  30 -- 0  0  80 100                                                                               70                         Crabgrass 0  95 0  0  0  10 90 20 0  -- 0  40 95 80 50                         Downy Brome                                                                              0  45 0  0  0  10 0  0  0  0  0  10 35 70 30                         Giant foxtail                                                                            10 95 60 -- 0  0  95 25 0  80 30 30 85 95 80                         Italn. Rygrass                                                                           0  85 0  0  0  0  60 0  0  10 30 55 90 90 85                         Johnsongrass                                                                             20 85 0  10 0  10 75 0  0  10 0  20 95 90 80                         Lambsquarter                                                                             100                                                                               100                                                                               20 50 10 0  100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               95 100                                                                               100                                                                               100                        Morningglory                                                                             0  -- 40 30 0  40 65 10 40 30 10 50 90 75 80                         Rape      0  95 0  20 0  0  25 0  0  0  10 0  100                                                                               100                                                                               85                         Redroot Pigweed                                                                          100                                                                               100                                                                               100                                                                               0  90 60 100                                                                               95 100                                                                               100                                                                               100                                                                               80 100                                                                               100                                                                               100                        Soybean   20 55 0  0  0  0  10 0  10 10 0  0  15 100                                                                               0                          Speedwell 10 100                                                                               0  75 0  -- 30 20 90 -- 100                                                                               -- 100                                                                               100                                                                               100                        Sugar beet                                                                               20 100                                                                               30 25 0  0  95 0  30 85 0  0  100                                                                               100                                                                               100                        Velvetleaf                                                                               100                                                                               100                                                                               0  70 10 20 100                                                                               90 80 100                                                                               30 80 100                                                                               100                                                                               100                        Wheat     0  40 0  0  0  0  20 10 0  0  0  40 80 90 75                         Wild buckwheat                                                                           0  80 10 0  0  0  100                                                                               0  30 10 0  30 70 100                                                                               90                         Wild oat  20 65 0  10 10 0  45 0  0  25 35 50 70 90 80                         __________________________________________________________________________                COMPOUND                                                            Rate 16 g/ha                                                                              1  2  9  18 22 23 29 33 34 35 36 41 42  43                          __________________________________________________________________________     POSTEMERGENCE                                                                  Barley Igri                                                                               -- 45 10 25 20 50 50 45 55 50 40 45 40  35                          Barnyard 2 10 60 0  0  0  55 30 45 40 20 30 20 100 0                           Barnyardgrass                                                                             -- 65 0  25 15 80 40 50 60 40 30 0  95  70                          Bedstraw   -- 100                                                                               0  25 10 95 75 60 100                                                                               70 75 95 100 --                          Blackgrass -- 45 0  0  0  50 40 35 70 40 65 30 75  60                          Chickweed  -- 95 0  40 50 80 75 75 90 65 95 90 95  70                          Cocklebur  -- 90 0  50 50 90 80 90 90 60 70 50 100 85                          Corn       -- 50 10 20 20 25 25 25 25 30 25 35 65  60                          Cotton     -- 100                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100 100                         Crabgrass  -- 75 0  20 10 55 -- 20 30 20 20 45 70  30                          Downy Brome                                                                               -- 65 0  0  0  55 30 50 70 50 70 20 55  25                          Duck salad 0  0  0  0  0  0  0  0  0  0  0  0  0   0                           Giant foxtail                                                                             -- 95 0  40 30 75 40 50 40 30 35 55 80  55                          Italn. Rygrass                                                                            -- 70 0  0  0  45 55 65 65 40 70 45 80  45                          Johnsongrass                                                                              -- 90 0  60 20 70 35 50 40 30 60 40 90  85                          Lambsquarter                                                                              -- 100                                                                               40 40 50 100                                                                               100                                                                               95 100                                                                               90 100                                                                               65 95  70                          Morningglory                                                                              -- 100                                                                               45 85 70 100                                                                               100                                                                               95 100                                                                               90 90 95 100 90                          Rape       -- 100                                                                               50 80 0  100                                                                               75 100                                                                               65 90 90 100                                                                               100 85                          Redroot Pigweed                                                                           -- 100                                                                               40 100                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               85 100                                                                               80 100 --                          Rice       35 80 10 0  0  50 35 45 50 10 35 30 45  0                           Soybean    -- 90 20 50 50 85 60 50 95 -- 70 80 80  70                          Speedwell  -- 100                                                                               0  100                                                                               40 100                                                                               -- 100                                                                               100                                                                               70 95 -- 100 100                         Sugar beet -- 100                                                                               20 50 65 100                                                                               100                                                                               100                                                                               100                                                                               95 90 95 100 100                         Umbrella sedge                                                                            0  0  0  0  0  0  0  20 0  0  0  0  0   0                           Velvetleaf -- 100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               100 100                         Watergrass 2                                                                              10 30 0  20 25 45 15 40 40 25 40 20 10  0                           Wheat      -- 35 10 30 35 35 35 45 40 40 45 45 50  30                          Wild buckwheat                                                                            -- 100                                                                               45 0  30 100                                                                               65 100                                                                               100                                                                               85 90 70 100 95                          Wild oat   -- 55 10 20 0  50 65 50 70 60 60 25 85  55                          PREEMERGENCE                                                                   Barley Igri                                                                               0  0  0  0  0  30 0  0  0  0  10 0  50  10                          Barnyardgrass                                                                             15 90 10 0  0  85 0  0  0  0  0  70 95  30                          Bedstraw   0  100                                                                               0  0  0  0  0  0  50 0  0  100                                                                               100 90                          Blackgrass 0  55 0  0  0  45 10 0  0  0  0  20 80  50                          Chickweed  0  25 0  0  0  100                                                                               0  0  10 0  0  95 95  35                          Cocklebur  0  40 0  0  0  10 0  0  10 0  0  0  25  0                           Corn       0  35 0  0  0  10 0  0  0  0  0  30 35  40                          Cotton     0  35 0  0  0  30 0  20 30 -- 0  35 90  30                          Crabgrass  -- 95 0  0  0  90 20 0  20 0  30 55 70  50                          Downy Brome                                                                               0  40 0  0  0  0  0  0  0  0  10 10 30  10                          Giant foxtail                                                                             0  95 10 0  0  70 10 0  40 0  0  65 95  80                          Italn. Rygrass                                                                            0  75 0  0  0  30 0  0  0  20 40 70 70  45                          Johnsongrass                                                                              0  85 0  0  0  60 0  0  0  0  0  55 30  60                          Lambsquarter                                                                              100                                                                               100                                                                               30 0  0  100                                                                               100                                                                               65 100                                                                               90 95 100                                                                               100 100                         Morningglory                                                                              0  95 15 0  20 45 0  20 30 0  30 35 65  40                          Rape       0  100                                                                               15 0  0  0  0  0  0  0  0  100                                                                               90  30                          Redroot Pigweed                                                                           90 100                                                                               0  80 -- 100                                                                               50 85 85 10 -- 100                                                                               100 100                         Soybean    0  55 0  -- 0  0  0  0  0  0  0  0  35  0                           Speedwell  -- 100                                                                               40 0  10 30 0  90 90 100                                                                               95 100                                                                               100 100                         Sugar beet 0  100                                                                               10 0  0  60 0  10 -- 0  0  100                                                                               100 65                          Velvetleaf 30 100                                                                               15 0  10 100                                                                               20 70 90 10 20 100                                                                               85  30                          Wheat      0  35 0  0  0  20 10 0  0  0  40 25 40  20                          Wild buckwheat                                                                            0  70 0  0  0  70 0  0  10 0  0  65 100 65                          Wild oat   0  65 10 10 0  35 0  0  10 30 30 20 75  50                          __________________________________________________________________________                 COMPOUND                                                           Rate 8 g/ha 2    18  22  29  33  34  35  36  42   43                           __________________________________________________________________________     POSTEMERGENCE                                                                  Barley Igri 45   25  20  45  35  55  40  40  25   30                           Barnyard 2  20   0   0   0   40  35  0   25  100  0                            Barnyardgrass                                                                              60   25  0   30  50  50  35  30  65   40                           Bedstraw    100  25  0   35  55  95  50  65  80   60                           Blackgrass  45   0   0   40  30  65  40  30  65   55                           Chickweed   75   20  50  65  75  90  65  75  95   65                           Cocklebur   90   40  50  80  90  90  10  70  100  85                           Corn        50   10  10  20  20  15  20  20  50   25                           Cotton      100  100 90  90  100 100 100 95  100  100                          Crabgrass   70   15  0   15  20  20  10  15  65   30                           Downy Brome 40   0   0   10  35  70  50  40  30   20                           Duck salad  0    0   0   0   0   0   0   0   0    0                            Giant foxtail                                                                              80   30  20  35  35  30  25  30  35   25                           Italn. Rygrass                                                                             50   0   0   30  65  60  40  70  70   20                           Johnsongrass                                                                               75   55  15  30  50  30  30  60  35   70                           Lambsquarter                                                                               100  40  0   100 85  100 90  95  85   65                           Morningglory                                                                               100  80  70  90  95  85  90  85  --   80                           Rape        100  65  0   65  70  65  75  90  45   70                           Redroot Pigweed                                                                            100  85  80  90  100 100 70  100 100  100                          Rice        70   0   0   25  35  40  10  35  25   0                            Soybean     90   50  40  40  40  80  35  60  80   70                           Speedwell   100  100 40  95  100 95  65  95  100  95                           Sugar beet  100  50  20  100 95  100 70  90  100  80                           Umbrella sedge                                                                             0    0   0   0   0   0   0   0   0    0                            Velvetleaf  100  100 100 100 95  100 100 100 100  100                          Watergrass 2                                                                               10   0   25  0   25  10  --  40  10   0                            Wheat       35   20  30  30  30  30  35  10  30   20                           Wild buckwheat                                                                             100  0   30  --  100 100 65  90  100  90                           Wild oat    40   10  0   55  40  65  45  60  45   30                           PREEMERGENCE                                                                   Barley Igri 0    0   0   0   0   0   0   0   20   0                            Barnyardgrass                                                                              80   0   0   0   0   0   0   0   30   15                           Bedstraw    100  0   0   0   0   30  0   0   90   50                           Blackgrass  45   0   0   0   0   0   0   0   40   40                           Chickweed   25   0   0   0   0   0   0   0   70   --                           Cocklebur   20   0   0   0   0   10  0   0   10   0                            Corn        25   0   0   0   0   0   0   0   25   10                           Cotton      30   0   0   0   --  30  0   0   55   0                            Crabgrass   95   0   0   0   0   10  0   0   30   30                           Downy Brome 10   0   0   0   0   0   0   10  10   10                           Giant foxtail                                                                              90   0   0   10  0   30  0   0   85   70                           Italn. Rygrass                                                                             55   0   0   0   0   0   10  40  50   30                           Johnsongrass                                                                               85   0   0   0   0   0   0   0   30   10                           Lambsquarter                                                                               100  0   0   100 45  100 90  90  90   90                           Morningglory                                                                               50   0   10  0   10  30  0   10  65   20                           Rape        45   0   0   0   0   0   0   0   60   0                            Redroot Pigweed                                                                            100  0   50  --  45  70  0   20  100  60                           Soybean     50   0   0   0   0   0   0   0   35   0                            Speedwell   100  0   0   0   0   90  10  90  100  100                          Sugar beet  100  0   0   0   0   20  0   0   70   55                           Velvetleaf  100  0   0   0   20  25  0   0   70   10                           Wheat       0    0   0   0   0   0   0   40  10   0                            Wild buckwheat                                                                             55   0   0   0   0   0   0   0   70   10                           Wild oat    25   10  0   0   0   0   30  0   35   20                           __________________________________________________________________________                   COMPOUND                   COMPOUND                              Rate 4 g/ha   2      42     Rate 4 g/ha  2      42                             __________________________________________________________________________     POSTEMERGENCE               PREEMERGENCE                                       Barley Igri   45     25     Barley Igri  0      10                             Barnyard 2    --     100    Barnyardgrass                                                                               20     15                             Barnyardgrass 25     10     Bedstraw     0      30                             Bedstraw      80     0      Blackgrass   10     20                             Blackgrass    40     30     Chickweed    0      10                             Chickweed     60     75     Cocklebur    0      0                              Cocklebur     65     100    Corn         0      0                              Corn          25     20     Cotton       0      0                              Cotton        90     95     Crabgrass    85     30                             Crabgrass     30     30     Downy Brome  --     10                             Downy Brome   35     10     Giant foxtail                                                                               85     85                             Duck salad    --     0      Italn. Rygrass                                                                              45     30                             Giant foxtail 70     20     Johnsongrass 60     10                             Italn. Rygrass                                                                               35     30     Lambsquarter 100    85                             Johnsongrass  40     20     Morningglory 50     30                             Lambsquarter  100    65     Rape         0      30                             Morningglory  95     100    Redroot Pigweed                                                                             100    80                             Rape          100    30     Soybean      0      30                             Redroot Pigweed                                                                              100    100    Speedwell    --     80                             Rice          --     25     Sugar beet   60     10                             Soybean       80     60     Velvetleaf   100    20                             Speedwell     100    100    Wheat        0      0                              Sugar beet    100    50     Wild buckwheat                                                                              0      60                             Umbrella sedge                                                                               --     0      Wild oat     30     25                             Velvetleaf    100    100                                                       Watergrass 2  --     10                                                        Wheat         30     20                                                        Wild buckwheat                                                                               100    80                                                        Wild oat      40     25                                                        __________________________________________________________________________     Rate 2 g/ha     COMPOUND 2  Rate 2 g/ha   COMPOUND 2                           __________________________________________________________________________     POSTEMERGENCE               PREEMERGENCE                                       Barley Igri     40          Barley Igri   0                                    Barnyard 2      --          Barnyardgrass 0                                    Barnyardgrass   20          Bedstraw      0                                    Bedstraw        10          Blackgrass    10                                   Blackgrass      30          Chickweed     0                                    Chickweed       60          Cocklebur     0                                    Cocklebur       60          Corn          0                                    Corn            25          Cotton        0                                    Cotton          90          Crabgrass     65                                   Crabgrass       --          Downy Brome   0                                    Downy Brome     35          Giant foxtail 65                                   Duck salad      --          Italn. Rygrass                                                                               25                                   Giant foxtail   60          Johnsongrass  20                                   Italn. Rygrass  20          Lambsquarter  90                                   Johnsongrass    40          Morningglory  0                                    Lambsquarter    100         Rape          0                                    Morningglory    80          Redroot Pigweed                                                                              90                                   Rape            90          Soybean       0                                    Redroot Pigweed 100         Speedwell     --                                   Rice            --          Sugar beet    20                                   Soybean         35          Velvetleaf    90                                   Speedwell       100         Wheat         0                                    Sugar beet      100         Wild buckwheat                                                                               0                                    Umbrella sedge  --          Wild oat      20                                   Velvetleaf      100                                                            Watergrass 2    --                                                             Wheat           30                                                             Wild buckwheat  95                                                             Wild oat        40                                                             __________________________________________________________________________     Rate 1 g/ha     COMPOUND 2  Rate 1 g/ha   COMPOUND 2                           __________________________________________________________________________     POSTEMERGENCE               PREEMERGENCE                                       Barley Igri     40          Barley Igri   0                                    Barnyard 2      --          Barnyardgrass 0                                    Barnyardgrass   15          Bedstraw      0                                    Bedstraw        0           Blackgrass    10                                   Blackgrass      25          Chickweed     0                                    Chickweed       55          Cocklebur     0                                    Cocklebur       50          Corn          0                                    Corn            20          Cotton        0                                    Cotton          90          Crabgrass     30                                   Crabgrass       25          Downy Brome   0                                    Downy Brome     10          Giant foxtail 0                                    Duck salad      --          Italn. Rygrass                                                                               10                                   Giant foxtail   35          Johnsongrass  20                                   Italn. Rygrass  10          Lambsquarter  40                                   Johnsongrass    40          Morningglory  0                                    Lambsquarter    85          Rape          0                                    Morningglory    50          Redroot Pigweed                                                                              90                                   Rape            90          Soybean       0                                    Redroot Pigweed 90          Speedwell     --                                   Rice            --          Sugar beet    0                                    Soybean         35          Velvetleaf    50                                   Speedwell       100         Wheat         0                                    Sugar beet      80          Wild buckwheat                                                                               0                                    Umbrella sedge  --          Wild oat      10                                   Velvetleaf      100                                                            Watergrass 2    --                                                             Wheat           10                                                             Wild buckwheat  75                                                             Wild oat        35                                                             __________________________________________________________________________

TEST D

Seeds, rhizomes, or plant parts of alfalfa (Medicago sativa), annual bluegrass (Poa annua), bermudagrass (Cynodon dactylon), broadleaf signalgrass (Brachiaria platyphylia), common purslane (Portulaca oleracea), common ragweed (Ambrosia artemisiifolia), dallisgrass (Paspalum dilatatum), field bindweed (Convolvulus arvensis), goosegrass (Eleusine indica), guineagrass (Panicum maximum), itchgrass (Rottboellia cochinchinensis), johnsongrass (Sorghum halepense), large crabgrass (Digitaria sanguinalis), peanut (Arachis hypoagaea), pitted morningglory (Ipomoea lacunosa), purple nutsedge (Cyperus rotundus), sandbur (Southern sandbur), smooth crabgrass (Digitaria ischaemum) were planted into greenhouse pots containing greenhouse planting medium. Each pot contained only one plant species.

The test compound was formulated in a non-phytotoxic solvent mixture which includes a surfactant and applied preemergence and/or postemergence to the plants. Preemergence applications were made within one day of planting the seeds or plant parts. Postemergence applications were applied when the plants were in the two to four leaf stage (three to twenty cm). Untreated control plants and treated plants were placed in the greenhouse and visually evaluated for injury at 14 to 28 days after herbicide application. Plant response ratings, summarized in Table D, are based on a 0 to 100 scale where 0 is no injury and 100 is complete control. A dash (-) response indicates no test result.

                  TABLE D                                                          ______________________________________                                                   COM-                 COM-                                                      POUND                POUND                                           Rate 0250 g/ha                                                                             2      41     Rate 0250 g/ha                                                                            2    41                                   ______________________________________                                         POSTEMERGENCE             PREEMERGENCE                                         Alfalfa Var.                                                                               65     20     Alfalfa Var.                                                                              95   50                                   Ann Bluegrass                                                                              60     0      Ann Bluegrass                                                                             90   35                                   Bermudagrass                                                                               20     30     Bermudagrass                                                                              100  98                                   Brdlf Sgnlgrass                                                                            80     95     Brdlf Sgnlgrass                                                                           100  98                                   Cmn Purslane                                                                               100    95     Cmn Purslane                                                                              100  100                                  Cmn Ragweed 100    100    Cmn Ragweed                                                                               100  100                                  Dallisgrass 75     20     Dallisgrass                                                                               100  100                                  Field Bindweed                                                                             98     100    Field Bindweed                                                                            100  100                                  Goosegrass  75     50     Goosegrass 100  100                                  Guineagrass 65     0      Guineagrass                                                                               100  100                                  Itchgrass   50     30     Itchgrass  95   60                                   Johnson grass                                                                              80     20     Johnson grass                                                                             100  35                                   Large Crabgrass                                                                            70     55     Large Crabgrass                                                                           100  98                                   Peanuts     65     40     Peanuts    20   50                                   Pit Morninglory                                                                            80     40     Pit Morninglory                                                                           85   80                                   Purple Nutsedge                                                                            --     80     Purple Nutsedge                                                                           50   35                                   Sandbur     75     50     Sandbur    95   65                                   Smooth Crabgras                                                                            60     30     Smooth Crabgras                                                                           98   98                                   ______________________________________                                                     COM-                   COM-                                                    POUND                  POUND                                       Rate 0125 g/ha                                                                             41        Rate 0125 g/ha                                                                              41                                          ______________________________________                                         POSTEMERGENCE         PREEMERGENCE                                             Alfalfa Var.                                                                               30        Alfalfa Var. 60                                          Ann Bluegrass                                                                              0         Ann Bluegrass                                                                               0                                           Bermudagrass                                                                               0         Bermudagrass 50                                          Brdlf Sgnlgrass                                                                            30        Brdlf Sgnlgrass                                                                             50                                          Cmn Purslane                                                                               70        Cmn Purslane 100                                         Cmn Ragweed 100       Cmn Ragweed  50                                          Dallisgrass 20        Dallisgrass  20                                          Field Bindweed                                                                             100       Field Bindweed                                                                              50                                          Goosegrass  20        Goosegrass   100                                         Guineagrass 20        Guineagrass  40                                          Itchgrass   40        Itchgrass    40                                          Johnson grass                                                                              0         Johnson grass                                                                               40                                          Large Crabgrass                                                                            0         Large Crabgrass                                                                             50                                          Peanuts     10        Peanuts      50                                          Pit Morninglory                                                                            10        Pit Morninglory                                                                             65                                          Purple Nutsedge                                                                            --        Purple Nutsedge                                                                             25                                          Sandbur     0         Sandbur      30                                          Smooth Crabgras                                                                            0         Smooth Crabgras                                                                             30                                          ______________________________________                                    

TEST E

Seeds of barnyardgrass (Echinochloa crus-galli), bindweed (Concolculus arvensis), black nightshade (Solanum ptycanthum dunal), cassia (Cassia obtusifolia), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutam), crabgrass (Digitaria spp.), fall panicum (Panicum dichotomiflorum), giant foxtail (Setaria faberii), green foxtail (Setaria viridis), jimsonweed (Datura stramonium), johnsongrass (Sorghum halepense), lambsquarter (Chenopodium album), morningglory (Ipomoea spp.), pigweed (Amaranthus retroflexus), prickly sida (Sida spinosa), ragweed (Ambrosia artemisiifolia), shattercane (Sorghum vulgare), signalgrass (Brachiaria platyphylla), smartweed (Polygonum pensylvanicum), soybean (Glycine max), sunflower (Helianthus annuus), velvetleaf (Abutilon theophrasti), wild proso (Pancium miliaceum), woolly cupgrass (Eriochloa villosa), yellow foxtail (Setaria lutescens) and purple nutsedge (Cyperus rotundus) tubers were planted into a matapeake sandy loam soil. These crops and weeds were grown in the greenhouse until the plants ranged in height from two to eighteen cm (one to four leaf stage), then treated postemergence with the test chemicals formulated in a non-phytotoxic solvent mixture which includes a surfactant. Pots receiving preemergence treatments were planted immediately prior to test chemical application. Pots treated in this fashion were placed in the greenhouse and maintained according to routine greenhouse procedures.

Treated plants and untreated controls were maintained in the greenhouse approximately 14-21 days after application of the test compound. Visual evaluations of plant injury responses were then recorded. Plant response ratings, summarized in Table E, are reported on a 0 to 100 scale where 0 is no effect and 100 is complete control.

    ______________________________________                                         Table E   COMPOUND   Table E     COMPOUND                                      Rate 70 g/ha                                                                              4         Rate 35 g/ha                                                                                4    42                                      ______________________________________                                         POST-                POST-                                                     EMERGENCE            EMERGENCE                                                 Barnyardgrass                                                                            55         Barnyardgrass                                                                              40    45                                      Bindweed  45         Bindweed    30    100                                     Blk Nightshade                                                                           45         Blk Nightshade                                                                             35    45                                      Cassia    30         Cassia      25    95                                      Cocklebur 60         Cocklebur   35    95                                      Corn      50         Corn        35    70                                      Cotton    100        Cotton      100   100                                     Crabgrass 40         Crabgrass   35    25                                      fall Panicum                                                                             45         Fall Panicum                                                                               35    35                                      Giant Foxtail                                                                            40         Giant Foxtail                                                                              25    35                                      Green Foxtail                                                                            35         Green Foxtail                                                                              25    35                                      Jimsonweed                                                                               85         Jimsonweed  60    95                                      Johnson Grass                                                                            40         Johnson Grass                                                                              35    40                                      Lambsquarter                                                                             40         Lambsquarter                                                                               35    70                                      Morningglory                                                                             100        Morningglory                                                                               95    100                                     Nutsedge  20         Nutsedge    10    25                                      Pigweed   95         Pigweed     55    100                                     Prickly Sida                                                                             50         Prickly Sida                                                                               45    100                                     Ragweed   50         Ragweed     35    60                                      Shattercane                                                                              50         Shattercane 40    55                                      Signalgrass                                                                              30         Signalgrass 20    50                                      Smartweed 35         Smartweed   20    40                                      Soybean   85         Soybean     30    90                                      Sunflower 80         Sunflower   75    85                                      Velvetleaf                                                                               95         Velvetleaf  85    100                                     Wild Proso                                                                               45         Wild Proso  35    40                                      Woolly cupgrass                                                                          30         Woolly cupgrass                                                                            25    35                                      Yellow Foxtail                                                                           40         Yellow Foxtail                                                                             25    35                                      ______________________________________                                         Table E   COMPOUND   Table E     COMPOUND                                      Rate 17 g/ha                                                                              4      42     Rate 8 g/ha                                                                               4    42                                    ______________________________________                                         POST-                    POST-                                                 EMERGENCE                EMERGENCE                                             Barnyardgrass                                                                            25      30     Barnyardgrass                                                                            25    25                                    Bindweed  25      100    Bindweed  20    75                                    Blk Nightshade                                                                           20      35     Blk Nightshade                                                                           15    25                                    Cassia    15      55     Cassia    10    50                                    Cocklebur 20      65     Cocklebur 15    60                                    Corn      30      40     Corn      25    35                                    Cotton    85      100    Cotton    80    100                                   Crabgrass 25      20     Crabgrass 20    15                                    Fall Panicum                                                                             25      25     Fall Panicum                                                                             20    25                                    Giant Foxtail                                                                            25      30     Giant Foxtail                                                                            15    30                                    Green Foxtail                                                                            20      35     Green Foxtail                                                                            15    30                                    Jimsonweed                                                                               25      75     Jimsonweed                                                                               15    55                                    Johnson Grass                                                                            30      30     Johnson Grass                                                                            25    25                                    Lambsquarter                                                                             25      65     Lambsquarter                                                                             25    50                                    Morningglory                                                                             25      100    Morningglory                                                                             15    95                                    Nutsedge   0      20     Nutsedge   0    15                                    Pigweed   35      100    Pigweed   25    100                                   Prickly Sida                                                                             20      100    Prickly Sida                                                                             15    80                                    Ragweed   25      35     Ragweed   20    30                                    Shattercane                                                                              35      45     Shattercane                                                                              25    35                                    Signalgrass                                                                              15      45     Signalgrass                                                                              15    35                                    Smartweed 15      30     Smartweed 15    25                                    Soybean   30      75     Soybean   25    60                                    Sunflower 50      80     Sunflower 45    80                                    Velvetleaf                                                                               30      100    Velvetleaf                                                                               20    85                                    Wild Proso                                                                               25      35     Wild Proso                                                                               20    35                                    Woolly cupgrass                                                                          20      25     Woolly cupgrass                                                                          15    20                                    Yellow Foxtail                                                                           20      30     Yellow Foxtail                                                                           15    25                                    ______________________________________                                         Table E   COMPOUND   Table E     COMPOUND                                      Rate 4 g/ha                                                                               4      42     Rate 2 g/ha                                                                              42                                          ______________________________________                                         POST-                    POST-                                                 EMERGENCE                EMERGENCE                                             Barnyardgrass                                                                            15      25     Barnyardgrass                                                                            15                                          Bindweed  15      65     Bindweed  15                                          Blk Nightshade                                                                           10      20     Blk Nightshade                                                                           15                                          Cassia     0      45     Cassia    30                                          Cocklebur 10      55     Cocklebur 25                                          Corn      25      30     Corn      25                                          Cotton    75      100    Cotton    100                                         Crabgrass 20      10     Crabgrass  0                                          Fall Panicum                                                                             10      15     Fall Panicum                                                                             10                                          Giant Foxtail                                                                            10      25     Giant Foxtail                                                                            20                                          Green Foxtail                                                                            10      25     Green Foxtail                                                                            20                                          Jimsonweed                                                                               10      50     Jimsonweed                                                                               45                                          Johnson Grass                                                                            20      20     Johnson Grass                                                                            15                                          Lambsquarter                                                                             20      45     Lambsquarter                                                                             35                                          Morningglory                                                                             10      95     Morningglory                                                                             35                                          Nutsedge   0      10     Nutsedge   0                                          Pigweed   15      100    Pigweed   100                                         Prickly Sida                                                                             10      75     Prickly Sida                                                                             20                                          Ragweed   15      30     Ragweed   25                                          Shattercane                                                                              20      35     Shattercane                                                                              25                                          Signalgrass                                                                              10      30     Signalgrass                                                                              25                                          Smartweed 10      20     Smartweed 10                                          Soybean   20      50     Soybean   45                                          Sunflower 30      75     Sunflower 70                                          Velvetleaf                                                                               10      80     Velvetleaf                                                                               40                                          Wild Proso                                                                               20      25     Wild Proso                                                                               20                                          Woolly cupgrass                                                                          10      15     Woolly cupgrass                                                                          10                                          Yellow Foxtail                                                                           15      25     Yellow Foxtail                                                                           25                                          ______________________________________                                    

TEST F

Compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which includes a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Test compounds were applied within approximately one day after planting seeds for the preemergence test.

Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include winter barley (Hordeum vulgare cv. `Igri`), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), downy brome (Bromus tectorum), galium (Galium aparine), green foxtail (Setaria viridis), kochia (Kochia scoparia), lambsquarters (Chenopodium album), speedwell (Veronica persica), ryegrass (Lolium multiflorum), sugar beet (Beta vulgaris cv. `US1`), sunflower (Helianthus annuus cv. `Russian Giant`), spring wheat (Triticum aestivum cv. `ERA`), windgrass (Apera spica-venti), winter wheat (Triticum aestivum cv. `Talent`), wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis) and wild oat (Avena fatua).

Blackgrass, galium and wild oat were treated at two growth stages. The first stage (1) was when the plants had two to three leaves. The second stage (2) was when the plants had approximately four leaves or in the initial stages of tillering. Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table F, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) means no test result.

    ______________________________________                                         Table F   COMPOUND    Table F     COMPOUND                                     Rate 125 g/ha                                                                            23          Rate 125 g/ha                                                                              23                                           ______________________________________                                         POST-                 PRE-                                                     EMERGENCE             EMERGENCE                                                Blackgrass (2)                                                                           80          Blackgrass (2)                                                                             50                                           Chickweed 100         Chickweed   100                                          Downy brome                                                                              40          Downy brome 50                                           Galium (2)                                                                               100         Galium (2)  100                                          Green foxtail                                                                            --          Green foxtail                                                                              100                                          Kochia    100         Kochia      80                                           Lambsquarters                                                                            100         Lambsquarters                                                                              100                                          Ryegrass  85          Ryegrass    75                                           Speedwell 100         Speedwell   100                                          Wheat (Spring)                                                                           50          Wheat (Spring)                                                                             70                                           Wheat (Winter)                                                                           35          Wheat (Winter)                                                                             35                                           Wild buckwheat                                                                           100         Wild buckwheat                                                                             100                                          Wild mustard                                                                             100         Wild mustard                                                                               100                                          Wild oat (2)                                                                             55          Wild oat (2)                                                                               70                                           Windgrass 100         Windgrass   100                                          Winter Barley                                                                            20          Winter Barley                                                                              20                                           ______________________________________                                         Table F   COMPOUND   Table F     COMPOUND                                      Rate 62 g/ha                                                                              2      23     Rate 62 g/ha                                                                             23                                          ______________________________________                                         POST-                    PRE-                                                  EMERGENCE                EMERGENCE                                             Blackgrass (2)                                                                            5      45     Blackgrass (2)                                                                           50                                          Chickweed 100     95     Chickweed 70                                          Downy brome                                                                               5      20     Downy brome                                                                              40                                          Galium (2)                                                                               100     90     Galium (2)                                                                               100                                         Green foxtail                                                                            100     --     Green foxtail                                                                            100                                         Kochia    100     100    Kochia    55                                          Lambsquarters                                                                            100     100    Lambsquarters                                                                            100                                         Ryegrass  20      15     Ryegrass  60                                          Speedwell 100     100    Speedwell 100                                         Wheat (Spring)                                                                           50      40     Wheat (Spring)                                                                           65                                          Wheat (Winter)                                                                           20      35     Wheat (Winter)                                                                           35                                          Wild buckwheat                                                                           100     100    Wild buckwheat                                                                           70                                          Wild mustard                                                                             100     100    Wild mustard                                                                             100                                         Wild oat (2)                                                                             30      40     Wild oat (2)                                                                             50                                          Windgrass 60      75     Windgrass 100                                         Winter Barley                                                                            20      20     Winter Barley                                                                            10                                          ______________________________________                                         Table F   COMPOUND   Table F     COMPOUND                                      Rate 31 g/ha                                                                              2      23     Rate 31 g/ha                                                                             23                                          ______________________________________                                         POST-                    PRE-                                                  EMERGENCE                EMERGENCE                                             Blackgrass (2)                                                                            5      20     Blackgrass (2)                                                                           30                                          Chickweed 100     65     Chickweed 40                                          Downy brome                                                                               0      20     Downy brome                                                                              10                                          Galium (2)                                                                               100     100    Galium (2)                                                                               100                                         Green foxtail                                                                            70      --     Green foxtail                                                                            100                                         Kochia    100     100    Kochia    50                                          Lambsquarters                                                                            100     100    Lambsquarters                                                                            100                                         Ryegrass   5      15     Ryegrass  45                                          Speedwell 100     100    Speedwell 100                                         Wheat (Spring)                                                                           20      35     Wheat (Spring)                                                                           10                                          Wheat (Winter)                                                                           15      45     Wheat (Winter)                                                                            0                                          Wild buckwheat                                                                           100     100    Wild buckwheat                                                                           85                                          Wild mustard                                                                             100     100    Wild mustard                                                                             100                                         Wild oat (2)                                                                             20      25     Wild oat (2)                                                                             35                                          Windgrass 20      75     Windgrass 100                                         Winter Barley                                                                            10      20     Winter Barley                                                                             0                                          ______________________________________                                         Table F   COMPOUND   Table F     COMPOUND                                      Rate 16 g/ha                                                                              2      23     Rate 16 g/ha                                                                             23                                          ______________________________________                                         POST-                    PRE-                                                  EMERGENCE                EMERGENCE                                             Blackgrass (2)                                                                            5      15     Blackgrass (2)                                                                            0                                          Chickweed 100     70     Chickweed 40                                          Downy brome                                                                               0      20     Downy brome                                                                               0                                          Galium (2)                                                                               60      100    Galium (2)                                                                               35                                          Green foxtail                                                                            70      --     Green foxtail                                                                            95                                          Kochia    100     60     Kochia    50                                          Lambsquarters                                                                            40      98     Lambsquarters                                                                            100                                         Ryegrass  5       15     Ryegrass  10                                          Speedwell 100     100    Speedwell 100                                         Wheat (Spring)                                                                           20      30     Wheat (Spring)                                                                           15                                          Wheat (Winter)                                                                           15      35     Wheat (Winter)                                                                            0                                          Wild buckwheat                                                                           60      60     Wild buckwheat                                                                           100                                         Wild mustard                                                                             100     100    Wild mustard                                                                             100                                         Wild oat (2)                                                                             15      20     Wild oat (2)                                                                             10                                          Windgrass  5      35     Windgrass 95                                          Winter Barley                                                                            10      20     Winter Barley                                                                             0                                          ______________________________________                                         Table F   COMPOUND   Table F     COMPOUND                                      Rate 8 g/ha                                                                               2         Rate 4 g/ha  2                                            ______________________________________                                         POST-                PRE-                                                      EMERGENCE            EMERGENCE                                                 Blackgrass (2)                                                                            5         Blackgrass (2)                                                                              5                                            Chickweed 80         Chickweed   60                                            Downy brome                                                                               0         Downy brome  0                                            Galium (2)                                                                               50         Galium (2)  --                                            Green foxtail                                                                            30         Green foxtail                                                                               5                                            Kochia    30         Kochia       5                                            Lambsquarter                                                                             --         Lambsquarters                                                                               0                                            Ryegrass  5          Ryegrass     5                                            Speedwell 100        Speedwell   100                                           Wheat (Spring)                                                                           15         Wheat (Spring)                                                                             10                                            Wheat (Winter)                                                                           15         Wheat (Winter)                                                                             10                                            Wild buckwheat                                                                           10         Wild buckwheat                                                                             --                                            Wild mustard                                                                             100        Wild mustard                                                                               80                                            Wild oat (2)                                                                             10         Wild oat (2)                                                                               10                                            Windgrass 5          Windgrass    5                                            Winter Barley                                                                            10         Winter Barley                                                                              10                                            ______________________________________                                     

What is claimed is:
 1. A compound Formulae I ##STR36## wherein Q is ##STR37## R¹ is independently hydrogen; halogen or C₁ -C₃ alkyl; R² is independently hydrogen; fluorine; chlorine; or bromine;V is O or S; m is 1 or 2; p is 0 or 1 provided that when m is 2, then p is 0; W is O or S; R³ is halogen; R⁴ is H; C₁ -C₈ alkyl; C₁ -C₈ haloalkyl; halogen; OH; OR⁹ ; SH; S(O)_(n) R⁹ ; COR⁹ ; CO₂ R⁹ ; C(O)SR⁹ ; C(O)NR¹¹ R¹² ; CHO; CR¹¹ ═NOR¹⁸ ; CH═CR¹⁹ CO₂ R⁹ ; CH₂ CHR¹⁹ CO₂ R⁹ ; CO₂ N═CR¹³ R¹⁴ ; NO₂ ; CN; NHSO₂ R¹⁵ ; NHSO₂ NHR¹⁵ ; NR⁹ R²⁰ ; NH₂ or phenyl optionally substituted with R²¹ ; n is 0, 1 or 2; R⁵ is C₁ -C₂ alkyl; C₁ -C₂ haloalkyl; OCH₃ ; SCH₃ ; OCHF₂ ; halogen; CN or NO₂ ; R⁶ is H; C₁ -C₃ alkyl or halogen; R⁷ is H; C₁ -C₃ alkyl; halogen; C₁ -C₃ haloalkyl; cyclopropyl; vinyl; C₂ alkynyl; CN; C(O)R²⁰ ; CO₂ R²⁰ ; C(O)NR²⁰ R²² ; CR¹⁶ R¹⁷ CN; CR¹⁶ R¹⁷ C(O)R²⁰ ; CR¹⁶ R¹⁷ CO₂ R²⁰ ; CR¹⁶ R¹⁷ C(O)NR²⁰ R²² ; CHR¹⁶ OH; CHR¹⁶ OC(O)R²⁰ or OCHR¹⁶ OC(O)NR²⁰ R²² ; or when Q is Q-2, R⁶ and R⁷ can be taken together with the carbon to which they are attached to form C═O; R⁸ is H; C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₂ -C₆ alkoxyalkyl; C₃ -C₆ alkenyl; C₃ -C₆ alkynyl; C₄ -C₇ cycloalkylalkyl; ##STR38## R⁹ is C₁ -C₈ alkyl; C₃ -C₈ cycloalkyl; C₃ -C₈ alkenyl; C₃ -C₈ alkynyl; C₁ -C₈ haloalkyl; C₂ -C₈ alkoxyalkyl; C₂ -C₈ alkylthioalkyl; C₂ -C₈ alkylsulfinylalkyl; C₂ -C₈ alkylsulfonylalkyl; C₄ -C₈ alkoxyalkoxyalkyl; C₄ -C₈ cycloalkylalkyl; C₆ -C₈ cycloalkoxyalkyl; C₄ -C₈ alkenyloxyalkyl; C₄ -C₈ alkynyloxyalkyl; C₃ -C₈ haloalkoxyalkyl; C₄ -C₈ haloalkenyloxyalkyl; C₄ -C₈ haloalkynyloxyalkyl; C₆ -C₈ cycloalkylthioalkyl; C₄ -C₈ alkenylthioalkyl; C₄ -C₈ alkynylthioalkyl; C₁ -C₄ alkyl substituted with phenoxy or benzyloxy, each ring optionally substituted with halogen, C₁ -C₃ alkyl or C₁ -C₃ haloalkyl; C₄ -C₈ trialkylsilylalkyl; C₃ -C₈ cyanoalkyl; C₃ -C₈ halocycloalkyl; C₃ -C₈ haloalkenyl; C₅ -C₈ alkoxyalkenyl; C₅ -C₈ haloalkoxyalkenyl; C₅ -C₈ alkylthioalkenyl; C₃ -C₈ haloalkynyl; C₅ -C₈ alkoxyalkynyl; C₅ -C₈ haloalkoxyalkynyl; C₅ -C₈ alkylthioalkynyl; C₂ -C₈ alkylcarbonyl; benzyl optionally substituted with halogen, C₁ -C₃ alkyl or C₁ -C₃ haloalkyl; CHR¹⁶ COR¹⁰ ; CHR¹⁶ P(O)(OR¹⁰)₂ ; CHR¹⁶ P(S)(OR¹⁰)₂ ; P(O)(OR¹⁰)₂ ; P(S)(OR¹⁰)₂ ; CHR¹⁶ C(O)NR¹¹ R¹² ; CHR¹⁶ C(O)NH₂ ; CHR¹⁶ CO₂ R¹⁰ ; CO₂ R¹⁰ ; SO₂ R¹⁰ ; phenyl optionally substituted with R²¹ ; ##STR39## R¹⁰ is C₁ -C₆ alkyl; C₁ -C₆ haloalkyl; C₃ -C₆ alkenyl or C₃ -C₆ alkynyl; R¹¹ and R¹³ are independently H or C₁ -C₄ alkyl; R¹² and R¹⁴ are independently C₁ -C₄ alkyl or phenyl optionally substituted with halogen, C₁ -C₃ alkyl or C₁ -C₃ haloalkyl; or R¹¹ and R¹² are taken together along with the nitrogen to which they are attached to form a piperidinyl, pyrrolidinyl or morpholinyl ring, each ring optionally substituted with C₁ -C₃ alkyl, phenyl or benzyl; or R¹³ and R¹⁴ are taken together with the carbon to which they are attached to form C₃ -C₈ cycloalkyl; R¹⁵ is C₁ -C₄ alkyl or C₁ -C₄ haloalkyl; R¹⁶ and R¹⁷ are independently H or C₁ -C₅ alkyl; R¹⁸ is H, C₁ -C₆ alkyl, C₃ -C₆ alkenyl or C₃ -C₆ alkynyl; R¹⁹ and R²⁴ are independently H, C₁ -C₄ alkyl or halogen; or R⁹ and R¹⁹ are taken together as C₂ -C₃ alkylene; R²⁰, R²¹, and R²⁵ are independently H or C₁ -C₄ alkyl; R²² is C₁ -C₂ alkyl; C₁ -C₂ haloalkyl; OCH₃ ; SCH₃ ; OCHF₂ ; or CNand their corresponding N-oxides and agriculturally-suitable salts.
 2. A compound according to claim 1 whereinR¹ is hydrogen or halogen; R² is hydrogen; chlorine; or fluorine; R⁴ is H; C₁ -C₈ alkyl; C₁ -C₈ haloalkyl; halogen; OH; OR⁹ ; SH; S(O)_(n) R⁹ ; COR⁹ ; CO₂ R⁹ ; C(O)SR⁹ ; C(O)NR¹¹ R¹² ; CHO; CH═CHCO₂ R⁹ ; CO₂ N═CR¹³ R¹⁴ ; NO₂ ; CN; NHSO₂ R¹⁵ ; or NHSO₂ NHR¹⁵.
 3. A compound according to claim 2 whereinR² is hydrogen or fluorine; and R⁹ is C₁ -C₄ alkyl; C₃ -C₄ alkenyl; C₃ -C₄ alkynyl; C₂ -C₄ alkoxyalkyl; C₁ -C₄ haloalkyl; C₃ -C₄ haloalkenyl or C₃ -C₄ haloalkynyl.
 4. A compound according to claim 3 whereinQ is Q-1 or Q-5; R¹ and R² are each hydrogen; and R⁵ is halogen; CN; or NO₂.
 5. A compound according to claim 4 selected from the group:(±)-2- 4-chloro-2-fluoro-5-(2-propynyloxy)phenyl!tetrahydrocyclopropa 3,4!-pyrrolo 1,2-c!imidazole-1,3(2H,3aH)-dione and (±)-2- 4-chloro-2-fluoro-5- (1-methyl-2-propynyl)oxy!phenyl!tetrahydrocyclopropa 3,4!-pyrrolo 1,2-c!imidazole-1,3(2H,3aH)-dione.
 6. An herbicidal composition comprising an herbicidally effective amount of a compound according to claim 1 and an agriculturally suitable carrier.
 7. A method for controlling the growth of undesired vegetation comprising applying to the undesired vegetation or to the locus to be protected an herbicidally effective amount of a compound according to claim
 1. 